


NSFW Porn Gif (Long-Winded) Drabbles(ish) ft. The Brothers Winchester

by NaughtySammyBoy



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Ass Play, Come Eating, Cunnilingus, DIRRRRRTY TALK, Daddy Kink, Deep Throating, Dirty Talk, Double Penetration, F/M, Face-Fucking, Filthy, Hair-pulling, Jerking off of a particular Winchester, Multi, Oral Sex, Porn with Feelings, Real lube gets used at some point so don't you worry your pretty little head, Rough Sex, Smut, Spit As Lube, Spitroasting, Threesome, Use of a sex chair, Vaginal Fingering, Vaginal Sex, White button up of sex, You and the Winchesters say some nasty stuff, daddy!dean, light biting, so I'm adding the warning a second time
Language: English
Status: In-Progress
Published: 2020-05-22
Updated: 2020-10-26
Packaged: 2021-03-02 21:21:05
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 19
Words: 21,429
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24313438
Author URL: https://archiveofourown.org/users/NaughtySammyBoy/pseuds/NaughtySammyBoy
Summary: Porn gifs. Pure filth. Sweet lovin' thrown in along the way. Sam & Dean Winchester. What else does a girl need? ;)*warnings/tags will be added as chapters are uploaded* *adds (ish) to the title because apparently ya girl has no self-control when it comes to word count* *adds (Long-Winded) as well because wow some of these are actually bonafide one-shots* *tries not be immature about the word bonafied* *fails*
Relationships: Dean Winchester/Reader, Dean Winchester/You, Sam Winchester/Reader, Sam Winchester/Reader/Dean Winchester, Sam Winchester/You
Comments: 90
Kudos: 649





	1. Inside ft. Dean

Holy _shit_. 

You thought of this moment—this _exact_ moment—at least once a day since you friggin' met Dean Winchester. _A dirty thought a day keeps the doctor away_ —or whatever the fuck they say. You can't be hard-pressed to give a single valuable shit right now. 

Not when you've got Dean _inside_ you. That first push in—you almost died right there. You felt every single inch, dude. Every glorious, _glorious_ inch, filling you to the absolute brim. 

"Damn, you're _tight_ ," Dean breathes, like he's trying to pace himself. His green eyes flicker up to meet yours, and _bless him_ , he actually looks a little concerned. "Does that feel okay?" 

"You kiddin'?" You huff a small, incredulous laugh, reaching down to slide a few fingers over your clit, and _fuck_ , it's magical. "I don't think I've ever felt anything _better_." 

The blush that colors Dean's cheeks actually takes you by surprise. For someone who's cockier than hell in any other given circumstance, he's sure is a soft touch in the sack. It makes your heart grow three sizes behind your ribcage.

"C'mon, Dean," you smile saccherine-sweet up at him, chewing at your bottom lip as you slip your fingers down to brush over his you-slick cock where he's gently pulled a few inches back out. "Fuck me like you mean it, stud." 

He breathes a laugh of his own, snapping his hips forward in a jolt that makes you gasp, causes you to rub at your clit quickly in effort to keep up with the rhythm he finds. _Hell yeah_. You don't doubt for a single, solitary second that the first orgasm Dean Winchester gives you is about to ruin you for every man that comes after him. 

Which, come to think, may be none—because you might _actually_ grow a pair and tell him how you really feel, so you can lock him down for good. 

You'll worry about it later. Right now, there's a matter of getting fucked good and thorough that takes precedent—because _hello_. 

Dean frackin' Winchester is _finally_ inside you.


	2. Good Girl ft. Sam

"Fuck yeah," Sam breathes, looking down at where his thick cock is spreading you open. He relishes in the way the shaft glistens with the evidence of how wet you are, of how wet _he's_ made you. "Love watching you take me like this." 

"Sam," you whimper, hand tugging weakly on his wrist where he's got it wrapped around your knee to help keep you spread wide for him. He smiles, let's himself fall forward over you, enjoys that you just want him close. 

"So damn beautiful," Sam breathes, watching your face morphs with the pleasure he's providing, fucking into you the way he knows you like. "You feel so _good_ ," he husks, slotting his fingers through yours and pressing your hands down into the mattress. "You gonna come for me, baby?" He asks, feeling the way you've started to clench helplessly around him. "Gonna show me how good I'm making that sweet little pussy feel?" 

You can only manage a tiny, frantic nod in response, followed by a sexy little sob that makes Sam's cock throb in warning. 

"I'm gonna come for you, too," he tells you in a breathy voice, sinking his teeth into the meat of your bottom lip to tug playfully. "Let's come together, beautiful," he requests once he releases it, resting his sweat-slick forehead against yours and fucking you both towards the release he feels building. "I wanna feel you milk my cock, baby. _God_. You work me so good when you're coming, so let me have it, huh." 

You do—like the good girl Sam _knows_ you are.


	3. Buckle Up, Buttercup ft. Dean

__

_So good. So good. So good._

It's the only coherent thought you currently have. 

"Is this what you wanted, sweetheart?" Dean growls in your ear, shoving his hips against you, fucking you down into the gaudy floral motel bedding. "Me fucking you good and deep? Huh? You said you wanted to feel it tomorrow. That still what you want?" 

"Yes!" You cry, hand gripping around his shoulder and the other splaying out over his ribs, sweat-slick skin slipping against his. "Give it to me, Dean. C'mon, baby, don't you _dare_ hold back on me." 

Dean twists a hand of his own into your hair, dragging your head back, his mouth moving until it's sliding against yours. "That's my girl," he praises, driving his cock into you with a thrust more brutal than the ones before it. "Better buckle up," he smirks, loving your broken little moan, the green of his eyes just a halo around his lust-blown pupils as he stares down at your blissed-out face. "You're in for a helluva ride, baby. No stops along the way. Just you and me all night." 

"Fuck _yes_." 


	4. Your Eyes Hold Everything ft. Dean

_Gah_. The way he _looked_ at you. 

It's the same way he always looks at you when you get on top and sink down onto his cock; it's like you're the most perfect thing he's ever seen. His lids get heavy, drooping over the bright green, dark lashes framing his gaze so gorgeously, pink lips parting like he wants to say so many things. 

"You like that, Dean?" You question, keeping the eye contact, trying to ignore the way your voice has taken on an emotion-edged tremble. There's no denying the way your heart beats for him. "You love it when I ride you, don't you, baby?" 

His brows tilt desperately. "You _know_ I do," he whispers, _reverent_ , bringing a hand up to cradle your jaw, moving down to wrap it loosely around your throat, fingers getting lost in your hair. "You're so fuckin' _beautiful,_ sweetheart." 

You _whimper_. 

He's not saying it just because you've got his cock inside you or because you're naked—he's saying it because he _means_ it. He says it so much—has since you first told him how you felt, long before you ever took your clothes off for him—that you believe it whole-heartedly. You don't even doubt it anymore. 

The confidence you find in his gaze is just _one_ of the greatest things Dean Winchester has ever given you. 


	5. Nylon Musings ft. Sam

Sam just couldn't _take_ it anymore. 

He tried, okay? He really, _really_ fucking tried. (Okay, _okay_. In hindsight—he probably didn't try all that hard.) But the entire time the two of you were walking around that police station, on a quest for answers regarding your current case while dressed in your FBI get-ups, all he could think about were those _fucking stockings_ you were wearing. 

He _already_ had to sit through the torture of watching you slide them up your smooth legs back at the motel earlier while you got ready, utterly oblivious to his open starting as you smoothed out the delicate lace where it hugged mid- _supple_ -thigh. 

He honestly thought he was going to have to take a detour to the bathroom before heading out. 

And as if _that_ wasn't already enough to make him chub up embarrassingly in his slacks—he had to watch you traipse around while _wearing_ the fucking things! _Plus_ the tightest skirt he thinks has ever existed, _and_ a pair of black heels that made your calves flex attractively behind the sheer nylon every time you took a step.

It was absolutely, devastatingly _maddening_. 

So, you can't _really_ blame him for what he does when you guys finally make it back to the motel room hours later. 

"I'm about to do something that might just end up being really, _really_ catastrophically stupid," Sam warns you once the door clicks locked, damn near growling, watching your face morph with confusion. "If you don't want it, just say no and I'll stop—no harm, no foul. Promise." 

"Okay?" You reply carefully, drawing your shoulders up in question. 

Sam closes the gap between the two of you in three, big strides, cupping your jaw in his hands and tilting your head up to crash his hungry mouth down into yours. It shocks you, he notices the way you freeze, gasping sharply against his lips, throwing your hands up into the air like you suddenly don't know what to do with them. 

It takes you maybe four-point-five seconds to decide you want to kiss Sam back, hands now flying up to get lost in his long hair, fingers fisting tightly to use as leverage to drag his mouth even closer. Sam postively _melts_ , getting his own on your ass, greedily squeezing at you through your little skirt as he licks into your hot, willing mouth. 

It takes all of three minutes for the two of you to get butt-ass naked— _except_ for your stockings.

"These—" Sam husks, his lengthy fingers tracing along the lace sitting so prettily against your soft skin, "These are going to stay right where they are." 

His cock _throbs_ when you look up him through full lashes and whisper, "Anything you want, Sam." 

He gets you on your back, spread out so gorgeously on the squeaky mattress, using his mouth and fingers to get you ready for him. The keening, high-pitched sounds that leave your slack mouth beeline _straight_ to his groin, and it's not long before the curiosity of what you sound like when you're getting fucked open wins out over his hearty love for eating pussy until he can't breathe. 

He sits back on his knees, grips tightly around your lace-wrapped thighs and drags you down to meet him, pressing one leg back to spread you wide. With a loud shout of bliss, he sinks his whole cock inside you where you're wet and tight and flexing uncontrollably. _Goddamn perfection_ , he thinks as he quickly snaps his hips back and forth. 

You look better than any dream he's ever had of you; the real sight of you—laid out before him, bare and spread open, taking him like you were always meant to, breasts swaying in tune with his fast hips, pretty mouth singing his name—beats anything he could have ever _possibly_ thought up on his own.

There's this sweet, little pleading look in your lust-bright eyes where you look up at him, accompanied by your breathy, whimper-y mantra of, "Just like that. Fuck yes. Don't stop, don't stop, don't stop. Huh! Feels so fucking good, Sam. Just like that, baby." 

Great _fuck_. Sam's gonna come a lot quicker than he had anticipated. 

He's _already_ swelling up with warning, burying himself so magically deep into the slick clutch of your trembling cunt. He buckles in, wraps a hand around the back of your thigh to keep it pressed against your chest, fingers slipping over buttery-soft nylon, and fucks the two of you to a noisy, hip-jerking, eye-rolling, positively-earth-shattering, mutual orgasm. 

Sam _may_ or may _not_ have blacked out. 


	6. Office Spendings ft. Dean Smith

**Notes for the Chapter:**

> Lol this ain't a drabble. I got carried away 🤷🏼 (which is pretty on brand me for me tbh)

You'd been Dean Smith's personal assistant for nearly three years now. And in those three years, you'd learned plenty about him. 

He liked his coffee black most days, but would ask for just a splash of French vanilla creamer if he was feeling particularly daring. He hated being late, but he hated boring board room meetings even more. He liked his documents separated into stacks ranked by importance— _needs immediate attention, not as dire but_ _still too important to totally ignore_ , or _can absolutely wait_. He almost never went a day without having a salad for lunch, but would indulge in a sweet snack once a week between important sales calls—usually a piece of cherry pie from the bakery down the street from Sandover Bridge & Iron Inc. 

The most important thing about him, however, is that Dean Smith can just never seem to stop himself from calling you into his office and having his way with you—typically around three o'clock when most everyone on the floor's left for the day. 

Today is no different. 

"You got a little too loud yesterday, sweetheart," Dean says in a hot whisper, green eyes ablaze with hunger where they're locked with yours. His cock is out, jutting big and leaky-hard from the open fly of his slacks, and he's got your skirt rucked up around your waist and your panties pushed to the side. "You gonna be a good girl for me and be extra quiet today?" 

"Yes, sir," you nod eagerly, gasping when he notches the head of himself at your drooling hole. You sink your teeth down into your bottom lip when he starts pushing inside, trying your hardest to be silent as he stretches you out nice and wide. 

It's fucking _difficult_. Jesus. No one's ever filled you up this good before. 

"That's it," Dean praises the effort you're showing, voice sounding rougher now that he's buried to the hilt in your wet pussy. He grips your hips, tugging you forward so your ass hangs off the edge of his desk just a little bit more, giving him the advantage of a better angle. 

Then, he gets to _work_. 

The clothes you're both still wearing prove effective at dulling all of the sounds you rather enjoy when fully naked—the fleshy slap of his balls on your ass with every snap forward, or the crack of his hips meeting the backs of your thighs. Nonetheless, you don't need to hear them to know that your boss is fucking you good and hard. Plus, you can still _very_ much hear how wet you are—the squelch of his cock pistoning in and out of your weeping cunt making you _that_ much sloppier between the thighs. 

"I was gonna ask you earlier if you wouldn't mind goin' and getting me a slice of pie after lunch," Dean manages through his labored breathing, fingertips denting deeply into the fleshy globes of your ass. His eyes are downcast, watching himself disappear inside of you over and over again. "But then I remembered I had something so much sweeter right _here_ ," he explains, puncuating the statement by slamming right into that magical spot inside you. "Something that never fails to satisfy my appetite." 

Your mouth, soft and swollen-lipped from his earlier hungry kisses, falls open in a silent moan, brows knitting together in pleasure. _Fuck_. You want nothing more than to be able to scream for him, to tell him in desperate, pathetic sobs how impossibly good he feels—but he wants you to be a good, _obedient_ little assistant, stuffed full of his big, addictive cock and _quiet_. 

And even though you've remained utterly silent the whole time, Dean still curls a large, powerful hand around your mouth when you come, his fingers digging harshly into your cheek as he squeezes. It makes your head spin, eyes rolling back as your pussy flexes helplessly around him. 

Dean leans in, eyes lust-dark where they look into yours, his full, pillowy lips brushing his own knuckles. "Are you ready for your reward for being such a good girl for me?" He asks in a low, raspy voice, sounding so wonderfully wrecked that you ripple around his cock in anticipation, nodding weakly behind his hand and spreading your legs as wide at they'll go in this position. 

Dean's hips thunder between them, his bottom lip bitten between his perfectly straight teeth so tightly that it's totally blanched. He rocks himself to completion, filling you up to overflow with his hot, sticky spendings, mouth falling open in controlled silence and brows titled in desperate euphoria as he jerks through the pulsing waves of his release. 

"Jesus," he breathes once he's through the thick of it, face finding refuge pillowed upon your heaving breasts over your blouse as his hand falls away from your face, allowing you to pant openly. He raises his head again once he's got his breathing somewhat under control, pressing a firm, grateful kiss to your lips, distracting you with his talented mouth as he pulls his softening cock from you, his warm cum rushing out of your messy cunt and spilling down your crack. 

You giggle, high off fresh dopamine, eyes heavy-lidded as you watch Dean lift your left hand to his mouth. His parted lips ghost over the bump of the third knuckle, just above where an extravagant engagement ring sits, the fine-cut diamond dazzling in its sterling silver setting. 

"I still wonder what grouchy, _stuffy_ Mister Adler is going to have to say once he finds out that his most promising sales director asked his personal assistant to marry him," you smile, nuzzling into Dean's temple affectionately before pressing a soft kiss to his freshly-shaven cheek. You can still smell the spice of the after-shave that he used this morning. 

Dean hums happily in response, grin stretching his full lips as he says, "Ask me if I give two fucks." 


	7. Karma Sutra? Yeah, I know Her ft. Sam 'Is that a sex chair????' Winchester

**Notes for the Chapter:**

> I'mma just do y'all a solid and link the video these gifs are from because _fuck_. [Click here](https://www.pornhub.com/view_video.php?viewkey=ph597accf8babe2) to watch it. It doesn't have any audio but who the fuck needs it when it's this hot??? 
> 
> The guy's name is Jean Val Jean and really helps bring all my dirty Sam Winchester fantasies to life. 
> 
> You're welcome ;)
> 
> *sorry if the gifs are glitchy idk what's happening tbh but enjoy the sex

If someone had told you a few days ago that a— Wait. What did they call again? Oh, right—a _vengeful fucking spirit_ , because apparently, _yeah_ , those are an actual thing that exist. 

Anyway—

If someone had told you a few days ago that a vengeful spirit was going to reek havoc in the Manhattan high rise apartment that you _just_ signed a two-year lease for, you'd've thought they were missing a few marbles. 

Yet, here you were, standing in the open-plan layout of your fancy abode with two _large_ , flannel-wearing, gun-totin' men who just vamoosed the son of a bitch away. By _burning_ is fucking _bones_ after _digging up his grave._ Jesus. To say you were utterly and completely freaked out would be the understatement to end all understatements. 

The slightly-shorter-but-not-by-much one, Dean, gives you a smile and accepts the tight, grateful hug you give him. Then, he's heading towards the door, and the other one, Sam, still lingers near you and they must have had some type of conversation before returning to your apartment because Dean says, "I'll be in the car, Sammy." 

Then, it's just you and Sam. _Alone_. 

"Look, I don't mean to be nosy or inappropriate, and by all means, please stop me if I cross a line—" he looks adorably nervous, like he's scared you might actually flip on him for asking whatever it is he's about to ask. "But I, um, I'm just curious. Is...is that a tantra chair?" 

You follow the direction his eyes are cast in, landing on the curvy, wooden piece of furniture that's lined with red-leather padding. The one your ex-boyfriend bought you as an anniversary present a few years ago—the _only_ good thing to have come out of that entire relationship. It was a quite aesthetically pleasing peice, and not many people would even know it wasn't just a casual lounger, so that's why you have it sitting in the corner of your living room near the windows that overlook the Manhatten skyline. 

Cheeks heating, you look back at Sam and say, "Yeah, it is." And just in innocent curiosity, you ask, "Have, uh, you ever used one before?" 

Sam's cheeks go a little pink. "No," he answers, dimples popping with a smile made up entirely of trepidation and wonder. "I've only ever seen them in, er..." He stops, clears his throat awkwardly. 

"Porn?" You finish for him, unable to stop the smirk that curls your lips. You hum in amusement when he gives a slow nod, turning your head to look at the chair then back at him again, your brain forming an idea that your vagina can't seem to say yes loud enough to. 

Some sex would probably do you some good after the last few less-than-spectular days you've had. 

"I know I've already said thank you, like, a bajillion and one times for what you and your brother did, but—" You take a second to bite at your bottom lip, eyes flitting coquettishly between his. "Maybe I can interest you in a more _thorough_ show of thanks? I mean, if you want." 

Apparently Sam wants _really_ fucking bad.

It's not long before he's got you both naked and working you over in all types of different positions, easily aided by the ergonomic design of the chair. 

First, he kisses you stupid and breathless as you sit pressed chest-to-chest in the chair's dip, your thighs spread over his and your fingers lost in his hair as his tongue chases yours. Your eyes nearly roll back when he slides his mouth down the length of your neck, nibbling and sucking at various places that make your cunt throb eagerly in response. 

Next, after he's slipped off the chair, he kneels at the foot of it and effortlessly drags you down so he can eat your pussy from behind, nose-deep in your ass as an added bonus. He grasps at your backside with one big, callous-roughened hand and presses the other to the small of your back to anchor you in place, his slick, hot tongue slip-sliding through your dewy folds, drawing happy little sounds of pleasure from your smiling mouth. 

Once Sam's got you nice and sloppy-wet, he tells you to stay put and gets to his feet to slide the whole of his big, long cock into you, punching the air from your lungs and making you cry out shamelessly when he starts fucking you with quick snaps. There's a memorable moment when you give Sam a sexy little side-glance of appreciation and he sweetly sweeps a stray lock of hair away from your face, then proceeds to let you know how fucking phenomenal you feel around his cock. 

Your personal favorite of the passion-filled evening is when Sam decides to sit cross-legged; you in his lap, leaning back on your hands with one foot kicked up on the top of the chair and the other pointed on the floor. It leaves you postively spread open, giving Sam the awesome view of you rocking yourself on his cock, your clit smashing up against the well-kept thatch of hair at the base of him with every press forward. He makes sure to tell you how goddamn gorgeous he thinks you are when you come, your head tipping back momentarily in pure ecstacy when he gets his hands on your heaving chest while your cunt pulses rhythmically around him. 

The grand finale is something you'll defintely be getting off to for the remainder of your life—Sam bends you over the top ledge of the chair, your lower belly resting on the cushion that's there, and fucks you nice and easy. It's more a dirty, toe-tingling grind that has him so deep inside you, that you could cry tears of pure bliss. He gathers up your hair to tug just slightly before finally scooping it over your shoulder, getting it out of the way so he can mouth at your neck and shoulders, pressing hungry, sucking kisses to your skin as he palms and squeezes your breasts. 

When Sam finally comes, so do you, and it's honestly the hottest fucking thing you've ever been a part of. He shoves himself all the way up inside you as he unloads, hips pressed tightly to your ass, and spills the most breathtaking sounds into your ear. He's all sweat-slick against your back, helping the both of you through the pulsing aftershocks of your combined releases, arms crisscrossing around you as he licks some salt from your glistening skin. 

When your clothes are back in place, you give Sam your number, which he seems a little surprised by. 

"If you're ever in Manhattan again, don't hesitate to drop in," you tell him, biting down into your bottom lip in efforts to smother a giddy, I-just-got- _fucked_ smile. "I've got some other nice little items I think you'd really enjoy." 

Sam grins, boyishly handsome, and gives you one last, long-winded kiss goodbye. 

"Duly fuckin' noted, sweetheart." 

**Notes for the Chapter:**

> Did you make it this far or did you die halfway through like I did?


	8. Greedy ft. Sam & Dean

**Notes for the Chapter:**

> This is without a doubt the filthiest one yet. Just as a little warning; there's some really dirty, nasty shit in this chapter. I don't wanna spoil anything but just know—this probably ain't for the faint of heart...

"God, just look at her, Dean."

"Yeah, I see 'er, Sammy. Such a _greedy_ girl for us."

 _Gah_. With a brother at each end—Sam fucking deeply into your soaked cunt and Dean in your mouth with a hand wrapped around your hair—you felt totally and completely _insatiable_.

When you'd jokingly suggested a threesome as a way of celebrating yet another successful hunt, you had no idea the brothers would _actually_ jump at the idea. Nor did you think you'd end up being so fucking _hungry_ for them once the evening began. It was like you had this unquenchable thirst, just wanting more and more and _more_.

And well—Sam and Dean gave it to you without _any_ hesitation or reservation.

They were only two of the finest specimens you'd ever met, and with two large, gorgeous, _very_ well-endowed men at your disposal—you certainly can't blame a girl for being just a little gluttonous.

"Look so good with our cocks inside you, sweetheart," Dean praises, voice fallen to a deep rumble that made you clench around Sam, who lets loose one the sexiest moans you think you've ever heard.

"Fuck, _yeah_ ," he breathes, snapping his hips a bit harder, working himself in and out of the quivering clutch of your pussy. "Keep talkin' to her like that, De," he tells his brother, "Her sweet little pussy's tightening up so fuckin' _perfectly_."

Dean curls the hand that's not ponytailing your hair under your chin, tugging you off his cock with a sinful pop and tilting your head up so he can get a look at you. God, and you fucking _whimper_ as you stare up into his darkened eyes, the candy-apple green now just a mere halo around his pupils where they've blown wide with lust for you.

"You like when I talk dirty to you, princess?" He asks, leaning down to lick the spit from your swollen lips where it had dribbled out around his cock, taking just a second to lap filthily into your slack mouth. "You like when I tell you what a greedy, cock-hungry little girl you are? Like havin' Sam and me inside those _needy_ holes of yours, huh?"

Your mouth falls open, the moans of agreement that spill forth from of it resounding off the motel room walls. Sam's cock strikes against that spot inside you that sends you wailing in pleasure, thighs taking on a tremble you couldn't control even if you tried—the preamble to yet _another_ great orgasm you'll be having at the hands of the Brothers Winchesters.

You watch, brows titling in a desperate way, as Dean drags his pink-slick tongue up two of his thick fingers. "I'm just curious—" he husks, leaning over, and they must have shared some silent exchange because Sam's hands quickly move to spread your cheeks apart, and you die a new death when Dean slides his spit-soaked fingers over the sensitive furl of your asshole, "—if _this_ hole is just as greedy as the other two have proven to be."

You reward Dean's dirty curiosity by taking him back into your mouth, sliding your lips farther and farther down his pulsing shaft until you've got him nestled in your throat. As you gag noisily around him, Dean works a finger into your ass, going slow until you bloom open willingly for him to sink all the way in.

"Oh, she _likes_ that, Dean," Sam informs the room, no doubt feeling the way your pussy has started to grow more snug around his cock. "You want us to fuck you at the same time, baby? Get one cock in your sweet ass and the other in this perfect little cunt?" You roll your hips in response, wordlessly telling him _hell yes, Sam._ "Yeah, we'd fill you up _nice_ and full, leave you stuffed 'til you couldn't possibly take it anymore."

You tug your mouth away from Dean, turn your head to look over your shoulder at Sam, and say in a raspy sob, "Yes, fucking _give_ it to me. Use my greedy little fuck-holes. Make me take it."

"Holy _shit,_ sweetheart," Dean growls, now two-fingers-deep in your ass, and you postively _keen_ when Sam helps aid his older brother's passage by spitting directly on your now stretched out hole.

" _Dirty_ boy," you smile approvingly back at him, popping a few fingers into your mouth to get them wet and sloppy before moving your hand down between your legs. "You want me to come for you, Sam?" You ask him, voice turning into a breathy whimper now that you're playing with your clit. "You wanna see what my pussy feels like coming apart around your cock while Dean finger-fucks my tight little asshole?"

"Hell _yes_ ," Sam says, voice rough in his throat, hips moving with purpose now, the squishy, squelchy sounds of him fucking into you making your eyes roll in their sockets. His own eyes move down to admire the way you're spread open on his big cock, as well as where Dean's fingers flex and push into your ass. "Let me feel it, baby girl."

You come hard and _loud_ , frantically fucking yourself back onto Sam's cock and Dean's fingers, cunt and ass flexing rhythmically around them both. They praise you through it, working you higher and higher until you're shuttering and shaking through the aftershocks of your release.

It's too much but nearly enough at the same time, and you're left sobbing in your post-orgasm haze, still so desperate for more—for _them_ , for _all_ of it.

Dean coaxes your head up to give you a deep, mindnumbing kiss, drinking down your pathetic little cries, free hand that's not still down at your ass curled loosely around your throat. He pulls back, eyes heavy-lidded as they look deeply into yours, his full, pink lips parted as he pants wildly.

"We're not near finished with you just yet, sweetheart."

You gasp sharply when Sam pulls his glistening cock free, moving to climb off the bed and head towards his duffle. You take a moment to admire his naked form as he moves about, your cunt pulsing in the wake of his absence.

Cheeks filling with heat, you watch as Sam pulls a bottle of lube from one of the side pockets, his bottom lip bitten between his teeth when he turns to head back your way. He gives you filthy kiss upon his return to the fold, trailing his mouth down the line of your spine next and making you giggle when he playfully sinks his teeth into one of the fleshy globes of your backside.

You turn your gaze on Dean again, mouth going slack for a short moment when Sam pops the lid of the bottle and drizzles some slippery lube between your crack. The coolness slips down between the lips of your pussy, too, getting you utterly slick for what they have planned.

With an amorous little smile, you stare right into Dean's gorgeous eyes and say, " _Good_. Because I haven't had _nearly_ enough."

Like I said, can't blame a girl for being greedy—'specially when the Winchesters are involved.


	9. Blockbust-A-Nut ft. Dean

**Notes for the Chapter:**

> Lmao I laughed way too hard at the title...
> 
> Also, this another hella long "drabble" lolz I'm sorry (not really) but the Winchesters just bring out my inner freak, okay? That can't be summed up in 100 words or less. I tried. Okay. I didn't really, but whatever. 
> 
> Enjoy ;)

It was _supposed_ to be just another regular movie night.

Sam was out with Eileen, which left you and Dean on your own in the bunker. Not wanting to sit around getting drunk for the third night in a row, Dean suggested watching a _movie or sumthin'_ in the media room, and you agreed, telling him to grab some blankets and pillows while you headed to the kitchen to pop some corn and stock up on other unhealthy movie necessities.

It had started out innocently enough, okay?

You and Dean hunkered down on the couch in the media room just like you always did, surrounded by a nest of bed covers and fluffy pillows, chewing on cherry licorice whips as you searched for a movie to watch on one of the demand channels—yeah, you'd _actually_ talked the boys into springing for some decent cable—and mutually decided on one that seemed to have an interesting enough synopsis.

_Dylan Badder, Los Angeles' most ruthless crime detective, meets his match in the new partner the force pairs him up with. She's stubborn, opinionated, and just can't seem to stop fighting him on everything. How are they ever supposed to get along well enough to keep the City of Angels safe from the many dangers within it?_

It was listed as a thriller, and was shaping up to be a pretty good choice—when, all of sudden, _it_ happened; right there, in high definition splashed across the flatscreen anchored to the wall, Detective Dylan Badder was _giving it_ to his partner, the gorgeous and totally badass, Detective Marisol Hernández, in one of the most explicit sex scenes you'd ever seen in a freakin' _movie_ , for Christ's _sake._

It was all rough passion; I-can't-stand-you-sex in it's finest form, all grabby and shove-y, sprinkled with some intense eye contact and smoothly snapping hips. They got off together, _loudly_ , and you were unknowingly holding your breath just waiting for it be over al-frackin'- _ready._

Jesus. It went on _forever_. I mean, at least, it _felt_ like it did with Dean sitting beside you. Who, out of the corner of your eye, you saw lay an extra pillow over his lap once it was all said and done, clearing his throat and wiggling a bit on his ass to _readjust_ himself.

Thighs pressing together without your permission, you chanced a curious glance over at him, and well, Dean turned his head to look at you, too, and you both had _the look_ in your eyes.

You know the one. It's the one that says _I'm trying really, **really** hard not to be turned on right now but it's not fucking working out so well for me._

"You wouldn't want to, uh—"

"Yeah, totally. Like, I mean, I'm down if you are."

That's how you found yourself where you currently are; laid out on the couch on your back, butt-ass naked and legs spread wide, head propped up against the armrest, where Dean's got his hands anchored for leverage as he fucks into you, movie now nothing more than background noise to the sounds the two of you are releasing.

It might not be rough, tell-me-you-hate-me-sex like you just witnessed, but it doesn't make it any less fucking _passionate._

It feels so _good_ , and Dean gets himself so _deep_ with every foward push of his hips. He's hung as fuck and you just can't seem to stop telling him as much, the plethora of filth just spilling out of your kiss-swollen lips at its own accord.

"So big inside me, Dean," you whimper, looking up into his heavy-lidded, forest-green eyes, loving they way his ruddy lips part with noisy, labored breathing, his brows twisting in pleasure. "You fill my pussy up so good, baby. Oh, yes! _Just_ like that. Stretchin' me out so wide. God, yeah, you're gonna make me come again."

Dean watches, eyes fluttering as you open your mouth and stick out your tongue, using a few fingertips to gather up some spit that covers it, moaning shamelessly when you get your hand down to rub quick circles against your clit. He drops his gaze down to enjoy the show, voice a deep, rumbling husk when he says, "That's so fuckin' sexy, sweetheart."

You giggle, the sound of amusement quickly melting into a cry of euphoria when the head of his glorious cock nails that blasted spongy spot inside you. "There!" You gasp, only sounding a _tiny_ bit desperate, your hips flexing, searching for him when he pulls back again. He mimics the last thrust, nudging at you with a deadly accuracy that might just kill you before you reach the release just sitting on the cusp waiting for you. "Right there, Dean. _Fuck_. Keeping fucking me just like that. _Yeah_. Oh, my goodness. Don't stop, don't stop, don't stop..."

That mantra continues until your orgasm crests. The intensity that it hits with shocks you into silence, mouth falling open but omitting no sound, eyes rolling back in bliss as your hips jerk. Dean's a damn _champ_ , fucking you through it, not stopping until he's wrung every last morsel of pleasure from your sweat-glistened body.

Panting wildly, Dean eventually pulls his cock out, and through your post-orgasm hazy state of mind, you reach down and wrap your fingers around it, beating him to the punch. It's slippery with the evidence of your release, the noisy _schlick_ of it causing your cheeks to flame with warmth as your hand easily glides up and down the thick length of him in a tight-fisted jerk that makes his belly tremble. He moans your name in a way that has you throbbing happily between the legs, and you look up into his eyes and give him a playful smile.

"C'mon, Dean," you encourage, adding the thumbing over the leaky head of his cock to every tug upwards, and you watch the way his eyes cross for just a split second at the warmly welcomed addition. "Give it to me, baby," you say in a breathy, sluttish whisper, eyes full of pleading where they stay locked with his dazed ones, "Cover me in the nice, big load, Dean, I fucking _wan' it_."

And _boy_ , Dean Winchester sure is a _vocal_ one nearer to the end.

"Huh! _Ha_. Oh, _fuck_. I'm— _shit_. M'comin'." The first rope stripes across your belly, warm and wet on your skin, and you don't dare stop working his cock yet, enjoying the way his rocks into your fist. "Fuckin' hell. Feels so— H'oh _my_ —" The second one has a bit farther of a trajectory, painting your heaving breasts in pearly strings, and you notice that Dean's thighs are flexing in a mouthwatering way. "Oh, Jesus. _Yeah._ That's fuckin' _it_." The last one splurts onto your clit, slipping down between the swollen, ruddy lips of your pussy, then all the way down your crack—no doubt destined to leave a nice, questionable stain on the couch.

Dean nearly crumples down when you slow your hand to a sluggish pull, circling your thumb and forefinger around the ridge at the top of his cock and gently twisting over the head, grinning when one last, tiny drop leaks out to say hello. He's breathing harshly above you, and he watches, biting his bottom lip between his teeth, as you run your fingers through the cum coating your skin, listening to your satisfied little moans as you slide those same fingers into your mouth to taste him.

"Dirty girl," he breathes, reaching down to collect some on his fingers, too, smiling when you eagerly open your mouth for him and let him feed it to you. "So," he starts, sweeping his cum-coated fingertips across your tongue, "What'd'ya say we watch a sweet little rom-com next?"

You pull off his digits with a lewd pop and say with a frisky glint in your eyes, "As long you eat me out for the first half, then let me suck your cock for the second half."

"You've got yourself a deal, sweetheart."

"Shake on it?"

"How 'bout you just keep those pretty legs spread for me and let me get to work, yeah? Here, take the remote."

"What about _The Notebook_? Aw, they've got _Never Been Kissed_ on here."

"Don't care. Just pick one."

"Hey, don't get all bossy on—oh, _fuck_."

"You were saying?"

**Notes for the Chapter:**

> Y'all drop a comment below. They're my fav 💕😍


	10. Dessert Before Dinner ft. AU Lawyer!Husband!Sam

**Notes for the Chapter:**

> Le dreamy sigh. I love AU Sam as much as real-verse Sam loves giving head. Which is _a lot,_ I'll have you know. 
> 
> Does Sam's s3 dream about Bela ring any ~~clits~~ bells? No. Okay. [Allow me to refresh your memory.](https://youtu.be/DL0aaSFJxgE)
> 
> Unf.

You texted Sam during his lunch break to just check in on him—a quick and to-the-point _hey, handsome, hope everything's going okay. I so totally stinkin' love you._

The firm he worked for had a super high profile case that Sam was assigned the head lawyer on, and he'd been coming home wearier and grumpier than usual—but you understood and gave him whatever he needed. Whether it was food, sleep, a nice, hot relaxing bubble bath, or your totally willing, totally Sam-responsive body—

Whatever.

A frown darkened your face when you read his responding text; _Not so okay, just ready to be home._ But it lightens a little when he sends a second that says _I so totally stinkin' love you, too, beautiful._ And you positively giggle when he shoots you a third that reads _and by the way, the lunch you packed for me today was fan-fucking-tastic. Remind me to thank you properly later ;)_

At least he was feeling frisky.

However, the _not so okay_ part still didn't sit right with you and you decided that as a sweet little pick-me-up, you'd bake him a cake after you finish dinner. Made-from-scratch red velvet with sugar-coma-inducing buttercream frosting. You only ever made it on his birthday, but you thought it might help lighten whatever mood he came home in.

Later on that night, after you'd Suzy Homaker-ed a full pot roast dinner, you started whipping together the ingredients for the cake, shamelessly tasting the batter before dividing it into twin pans. You slipped them into the oven and then got to work on the buttercream, deciding to have a little more self-control with that one because you so _totally_ would lick the bowl clean if you didn't.

You're just finishing up frosting the cake when you hear the garage door whirring, then the side door opens in the distance and you listen for the three consecutive thuds—one for Sam's document-stuff briefcase where he drops it to floor by the door, then one for each of his fancy wingtips where he dramatically kicks them off like he does every night.

You're laughing to yourself and shaking your head when he sneaks up behind you, big hands sliding around your waist and chin tucking over your shoulder to see what you're doing.

"You _didn't,_ " Sam whispers, face turning into your neck so he can get his mouth on your skin.

"I most certainly _did_ ," you whisper back, gasping when he teethes at the sensitive spot just under the bolt of your jaw.

"But it's not my birthday," he husks in your ear, hands moving down, fingers flirting with the hem of the [strappy summer dress](https://dgzfssf1la12s.cloudfront.net/original/ee6dd513-c1b2-444e-9a38-3735fdfa08e6) you're wearing where it falls mid-thigh. When he finally creeps his touch under your skirt, a sound of surprise rises in his throat and he says in a heat-sweet voice, "Then again, maybe it _is_ my birthday. You naughty girl."

"It's the middle of July in _Texas_ ," you remind him, rocking your ass back into the cradle of his lap, feeling where he's started to fill, big and blood-hot, in his slacks. "You can't honestly expect me to wear unnecessary layers if I don't have to- _ohhh!"_

Your mini-rant is interrupted by Sam fingers—two _very_ long, _very_ talented fingers to be exact—slipping inside the wet clutch of your pussy. He can always get so _deep_ so _quickly_.

It still takes your breath away, even after all these years.

"Let's have a taste," Sam says, and you don't even to have to clarify what he's asking for. You just swipe your index finger through the frosting on the cake, lifting your hand up and back, sighing a happy little sound as your finger slips into Sam's hot, open mouth.

You turn your head to watch his tongue swirl around your fingertip, his lust-dark eyes locking with yours and his fingers flexing in your cunt, causing your mouth to fall open and brows to furrow in pleasure.

"So sweet," he murmurs, pulling his fingers out of you as he adds, "But I know something that's even _sweeter._ You wanna taste what it is?"

You nod, opening your mouth for him and keening when he slides his fingers, the same fingers he just had inside you, over your tongue. Lips closing around them, you suck the taste of yourself from his skin, shimmying your ass back against his confined cock.

"That's my girl," Sam smiles, pulling his fingers free and using them to grip your chin, titling your head to the side and crashing his mouth into yours, his tongue seeking entry. You grant it without hesitation, the flavors of you and the buttercream still sweet in Sam's mouth making for a downright _sinful_ combination. He pulls back once his had his fill, saying in a rumbly husk, "I think I need to taste for myself. Love tasting it on you, but I just want to be sure it's as sweet as I remember."

Hell _yes._

Sam spins you around and kneels at your feet, and you smile down at him and say in a foxy voice, "You're going to spoil your dinner, Mister Winchester."

"Not true at all," Sam smirks back hungrily, shoving the skirt of your tiny dress up and you reach down to gather it up into one of your hands, fisting it to the side against your hip as not to obstruct the spectacular view of your husband. "I'm a growing boy," he tells you, grabbing behind one of your knees to coax your leg up. You follow the tug, resting your foot on a barstool that's sitting just behind Sam and little to the side. "I can just eat and eat and _eat_. You know that better than anyone, Missus Winchester."

Breathing going a little labored, you asks with a coquettish smile, "Do I? I think you're going to have to remind me."

"It'd be my pleasure, beautiful," he tells you, positively _glowing_ , and you want to make a joke about it actually being _your_ pleasure but Sam's sudden nosedive into your pussy causes you to get all _distracted._ He hums into you as you cry out in pleasure, and the man acts like he's starved, tonguing eagerly through your folds to lap up the slick that's practically pouring out of you at this point.

"Yeah," you moan, looking down at where he's looking up at you, pupils blown wide like you're the best drug he could ever take. "You like that, huh? Eating my sweet, little pussy, tasting how wet you make me." His moan of approval vibrates against your tender skin, and you get your free hand in his hair, fingers tangling it to anchor yourself to his ravenous mouth. "God, you're so fucking _sexy._ "

The chuckle Sam breathes into you makes you gasp, and the sound only turns into more breathy, high-pitched sounds as he focuses the quick flick of his tongue on your clit, sucking occasionally just to hear the cute little hitch it causes in your throat. He knows how to get you there, and _fast,_ and it's not long at all before you're right there on the cusp, Sam's hands wrapped around your thigh where it's started to quake, fingers digging into the supple flesh.

"Fuck," you breathe, chest heaving, the foot still on the floor rising to its tiptoes and hips flexing in efforts get as close to Sam's skillful tongue as you possibly can. "You want me to come for you, Mister Winchester? Wanna drink up all that sweetness you've been waiting for?"

Sam's deep, rumbling, long _mhmmm_ is what finally tips the scales, and you moan noisily through the pulsing waves of the release you're thrown into, fingers tugging harshly at Sam's hair as your head falls back in bliss. He's moaning, too, shaking his head side-to-side between your legs, tongue lapping at you like you're dripping honey and he's got an insatiable sweet tooth, not stopping until you have to push his head away, spit-slick and sensitive and utterly _satisfied._

Sam stands to his full height, stepping between your legs and sinking his tongue into your mouth, letting you taste what he loves so much. It's a filthy, _dirty_ kiss, and you don't think you've ever loved a man more than you love your husband.

Sam pulls back, shadow-dusted chin still glistening with the evidence of how hard he made you come. "Whoever made up that rule about not eating dessert before dinner _obviously_ never ate a pussy as decadent and rich as yours," he grins, looking down at you lasciviously as he blows a chef's kiss, and you can't help but lean in, licking around his chin to clean him up, listening to the way it scritches under your hungry tongue.

"Still got room for dinner, big guy?" You ask once you're done, pressing a chaste, sickly-sugary kiss to his lips. "I made your favorite."

"Abso-friggin'-lutely," he says, heavy-lidded eyes staring so contently into yours. However, a wicked smirk soon overtakes his face. "Just prepare yourself, though, beautiful. Because I plan taking this here cake—" he points to your delicious masterpiece, "—and eating it off your body once we're finished with supper."

"Naughty man," you grin, wrapping your arms around his shoulders. "Don't you think you've already had enough dessert for one night?"

"Never," Sam husks, nose tipping against yours eskimo-style. "There's _always_ room for a second dessert."

"Whatever you say, Mister Winchester."

"Now, _that's_ what I like to hear."

"Shut _up_."

" _Make me_ , Missus Winchester."

"Oh, you'd like that _wouldn't_ you?"

"Hell yeah I would."

You have to reheat dinner by the time you two finally get around to eating. Neither one of you having any complaints about it, though.

Not a single one.


	11. Mercy Man ft. Dean

**Notes for the Chapter:**

> Lmao this didn't start out as a Daddy fic but I started looking more at the Dean gif below as I wrote and just couldn't help it. He just looks so fuckin' _Daddy_ , okay? 
> 
> Sorry if that's not your thang, but my vagina just couldn't be convinced to take this in any other direction. Oof. And my sincerest condolences to yo panties if it _is_ your kinda thang. Mine are ruined, too, friend. 
> 
> *shamessly daydreams about Daddy!Dean for the rest of the day*

You watch, perched on the ledge of the bed, propped back on your hands with one knee crossed over the other, as Dean moves about the motel room—in that _stupid_ white button-up that made heat clench around your insides every time he wore the damn thing.

"Dean?"

"Yeah, baby?"

He doesn't look up from his task of repacking his duffle as he acknowledges you, his brow screwed up in concentration as he tries to get everything to fit the way it did the first time he packed it. Sighing at his utter ignorance, you uncross your legs, letting the flowy skirt you're wearing drape between your thighs as you spread them.

" _Dean_."

" _What?"_ He questions, an agitated bite to his voice now, but he finally turns his head to look at you and his agitation instantly softens. His eyes flick down to look at your open stance, then up to your face where you're biting at your bottom lip, then back down again to see you playfully pull your knees back together and rub your thighs against one another. " _Oh_."

"Sam'll be gone a while checkin' that the coast is a hundo percent clear of any ghosties," you tell him, letting your gaze drag shamelessly up and down his impeccable form. "And we haven't had a minute to ourselves for the last week. Was just thinkin' of all the ways we could use it."

"Yeah?" Dean encourages you to continue, stalking over to you slow and swagger-sweet, stopping when his shins knock against your gathered knees.

"Yeah," you breathe, looking up him through your lashes, all faux innocence sprinkled over a naughty girl attitude. "I've missed you, Dean. _Need_ you."

"How much've you missed me, sweetheart? Just how bad do you need me right now?" He asks in a rough husk, eyes flaming green as he crouches down in front of you, sinking one hand into the mattress next to your hip and draping the other over one of your knees, wedging his thumb between the two. "If I slide a hand up this pesky skirt of yours, I am I gonna find my answer?"

Teeth sinking into your bottom lip to trap a keening moan, you let your eyes flutter in bliss for just a short moment before saying, "I can guarantee you'll find _more_ than enough evidence to prove what you do to me, Dean."

He hums in approval, full lips turning up into a wolfish smile. "Open up for me, then, baby," he commands, leaning forward a bit, which encourages you to do the same until your lips meet his in a gentle brush. "Let me see for myself, huh."

Feeling bold, you sink your teeth into the meat of his bottom lip as you spread your legs, listening to the guttural moan of surprise that falls from his mouth when you tug at it. A gasp filters out of yours when he snakes a hand up your inner thigh until his calloused fingertips brush your bare folds, teasing through them to testify how slick you are for him.

"You been panty-less all day?" Dean wonders, forehead tipping against yours so you're brow-to-brow as he drags circles around your clit, eyes casted down to watch the way your mouth falls open. He feels you nod a confirmation to his inquiry and says with a grin, "Only a naughty girl askin' for trouble would do somethin' like that."

" _Your_ naughty girl," you remind him, breathlessly reverent, rolling your hips down into his touch. "Make me come," you plead, "Please, Dean."

Much to your dismay—okay, not _really,_ though—Dean pulls his head back just far enough to stare into your eyes as he informs you in a tone you're all to familiar with that, "You're not coming until I'm inside you. But there's plenty of ground to cover before them, sweetheart. Think you can redeem yourself by being a good girl for me and not coming 'til you've got my cock in you?"

Fuck. Great and glorious _fuck._

When he pushes two thick fingers up into the heated clutch of your cunt, a desperately high-pitched moan flies out of your mouth and you nod frantically. " _Yes_ , Daddy," you tell him, staring right back into the darkened emerald that's got you pinned, "I can be a good girl for you. I _promise_ I will be."

Dean smirks in response, gaze trekking hungrily down your body until he's watching the way his wrist flexes between your wide-spread thighs, hand hidden beneath your skirt. "I don't believe you for one second, baby girl," he husks, white teeth sinking into the candy-pink of his lower lip. "You're _already_ clenchin' up. Maybe Daddy should show some mercy and let you come just this once, _then_ make you wait. Would you like that? Does my naughty girl need to come?"

"Fuck yeah, Daddy," you moan your approval, breath hitching in your throat when he smashes the pad of his thumb up against your clit as he curls his fingers deep inside you. "Oh, my _goodness_ ," you squeak, eyes crossing momentarily when he sweeps over that spot that makes your hips jerk in surprise.

God, you're so fucking close. Dean _knows_ it, too, and he knows _just_ what you need to send you hurtling off the ledge you're tipping precariously on.

So, he stares deeply into your pleasure-lidded eyes, wiggles his buried fingers quicker and says in a firm, perfectly controlled voice—

"Then _come_."

**Notes for the Chapter:**

> *comes*


	12. Handle It ft. Sam & Dean

**Notes for the Chapter:**

> *passes out menus* Can I interest anyone in some anal? Perhaps some dp action? How about some dirty talk to start everyone off with?

This was a first. 

Okay, no, not having a dick in your ass—you'd done that plenty. You were talking about the prospect of having one in your ass, then another in your cunt, all at _same_ time for the _first_ time _ever_ in your life. 

"Think you're gonna be able to handle the both of us, princess?" Dean smirks down at you, fucking himself into your delicately prepped asshole nice and steadily, looking down for a moment to admire the way he's got you stretched out around him. "Still confident these pretty little holes can take it?" 

With an eager nod, you reach down between your legs to rub at your clit, amplifying the pleasure that Dean strokes into you. Sam knees his way across the mattress seconds later and perches himself at your shoulder, and you immediately get a hand around his hard cock to stroke him loosely. He rewards you with a sultry grin that's handsome as hell, albeit upside-down from this angle.

"Sammy," Dean greets, pushing your foot towards his little brother like an offering of some kind, "Make yourself useful and hold her open for me, will ya?" 

Sam snickers but agrees, wordlessly wrapping his big, strong hand around one ankle and curling the fingers of the free one around the heel of your opposite foot. He pulls you open wider for Dean using the hold he's gained, making you keen approvingly and jack your hand up his cock a little tighter, turning your head to just briefly lick along the prominent vein that runs along the side of the velvety shaft. The spit that now covers him gives you a little bit smoother of a glide, and Sam let's you know how good it feels by rocking himself through your fist. 

"I want you to make yourself come for Dean before I get my cock into that perfect pussy of yours," he says, voice reduced to a rumble that comes from somewhere deep in his throat—the sexiest bedroom voice you've ever heard. It never fails to stoke the fire in your belly, makes you want him even more in an urgent sort of way that sends your head spinning. "Think you can do that for me, baby? Gonna keep playing with that little clit while Dean fills up your sweet ass over and over again?" 

Sam's dirty talk coupled with Dean's lube-slick cock deep inside you, plus the way you've started to rub desperate circles against yourself, has you hurtling towards the edge recklessly quick. "Yeah," you assure Sam in a breathy voice, looking down to watch the show between your legs, enjoying the way Dean's stomach clenches up every few thrusts, "That's not gonna be a problem whatso-freakin'-ever." 

The brothers share a moment of light laughter at that, faces soon falling into looks of lustful pride as they watch the way your body takes what they give you, and also what you give yourself. They've told you time and time again that you're the funnest, most adventurous, least bashful woman they've ever shared or even fucked respectively, and they always— _always_ —tell how much they enjoy you before, during, _and_ after—like they're your own personal hype team. In turn, they made you feel wanted and sexy and dangerously confident, like you could conquer the freakin' world if you wanted to—as long as you had them by your side. 

Tonight, however, you're conquering a much smaller task. The one they'd been preparing you for, one that the thought alone of made your heart pitter-patter embarrassingly fast behind your ribs. Tonight, you're taking both of them. Tonight, you're finally going to experience what it's like to have your boys inside you at the same time. They'd taken their time, had shown so much patience, took such great care to you to this point—you could cry real tears, you were so excited. 

"God, we love you like this, sweetheart," Dean's deep voice pulls you away from your soppy thoughts, his eyes so intensely green where they lock with yours as he fucks you. "You look so fucking beautiful spread out for us. Gonna make you feel so good. _Fuck._ Can't wait to see what you look like taking both of our cocks." 

You moan wantonly, feeling Sam's hands tighten where he's still holding open, easily keeping you in place even when your hips start flexing impatiently. 

"You want it, baby girl?" Dean questions, quickly quirking his own to shove the whole of his cock into your ass, making you gasp in surprise at the sudden fullness. "Wanna see what it's like to be split open by two big cocks?" 

You look up into his eyes through your lashes, face twisted up with pleasure as you work your clit quicker. "Yes," you cry and nod frantically, mouth falling open as he rhythmically pulses his hips, not pulling out a whole lot but just mostly letting you feel how good he fills you up. "Fuck _yes_ ," you clarify, voice high in pitch and desperation as you whisper-chant, "Give it to me. Give it to me. Give it to me." 

"You know what you gotta do, gorgeous," Sam reminds you, rubbing the leaky head of his cock over your slack mouth when you tip your head back. He slides between your lips when you open up even wider for him, your pink-slick tongue rolling out like an invitation he just can't say no to. "Come for us," he commands, fucking your mouth in earnest, his eyes rolling in bliss when he eventually breaches your welcoming throat. "Come for us so I can bury my cock inside that tight little pussy and fill you up to the fuckin' brim, baby." 

It builds until it explodes—your empty cunt spasming around nothing, your ass spasming around Dean, your fingers working yourself through it as you gag noisily around Sam, who soon pull his spit-soaked cock free to watch you gasp for air and sob with rapture. He releases one of your ankles, moves the now free hand down between your trembling thighs and swats yours away, unable to help himself as he pushes three fingers into your needy, sopping cunt to feel the way your muscles flex. 

"Fuck yeah, baby," he smiles rapaciously as he wiggles them in deeply, so hungry for you as you roll yourself down onto him and Dean, delirious with the twinges of aftershock that zip-zap through your pleasure-racked system. "You're so wet right now." 

"That's our girl," Dean adds in a low husk, grinding his hips in slow, dragging circles, hands splayed out on the backs of your thighs to keep you spread for them. "Always look like a dream comin' apart like that. Maybe I can talk you into lettin' me record you so you can see just how fucking good you look for us when you get off." 

"H'oh, my _gah_ ," you finally rasp pathetically, trying to catch your breath, which seems impossible as long they've got their cocks and fingers and hands on and in you. You're absolutely _feening_ , voice breathlessly, shamelessly wanton when you say, "I want it." 

Sam and Dean don't even _need_ clarification on what you mean. 

The brothers pull away, and Sam lays himself out on his back while you flip over onto your stomach, lifting yourself up to your hands and knees. A wolfish grin stretches your lips as you crawl towards him, slow and seductive, but the expression falls instantly when Dean presses a knee down into the mattress behind you and leans over to lay a heavy-handed slap to your ass. 

You gasp in surprise, looking back at him over your shoulder and smiling giddily through the sting it produces, then squealing with laughter when he pushes you towards Sam rather impatiently. The younger Winchester accepts you as you climb atop him, his hands locking around your waist as you rise up on your knees and reach between your legs to position his cock, your praises on his lips as you slide down the entire length of him in one slick, toe-curling descent. 

Dean crowds up behind you once you're fully seated, mouthing wetly at the space between shoulder and neck, hands overlapping his brother's on your hips. He moves his mouth up to your ear and commands in a throaty whisper, "Lean forward and spread yourself open for me." 

You sigh dreamily, falling over Sam and crushing your lips into his, kissing him with rapt hunger as you reach back and pull your asscheeks apart like Dean wants. The groan that the elder releases when you do makes you smile against Sam's mouth, because there's no doubt that Dean likes what he sees—your cunt stretched out around Sam and your other hole still gaping just a bit from moments before, practically shouting at Dean _fill me! fill me!_

The feeling of his blunt, lube-coated cockhead pressing against the furled rim of your asshole makes you pull your mouth away from Sam's, so you can moan out in approval. Sam sinks his fingers into your hair and thumbs at each temple, looking up into your pleasure-bright eyes as Dean starts pushing inside, not wanting to miss a single expression as you take them together for the first time. 

"That's it, baby," he breathes, gaze flicking down to watch they way your lips part with a wordless cry, then back up to watch your brows tilt in a desperate way, finally settling back on your eyes as he says, "Take us _just_ like that. Yeah. Nice and easy. Feels so good to have both holes stuffed, doesn't it, sweetheart?" 

"Ye—" you try to reply, but the declaration is cut off by a soft moan when Dean's hips finally kiss your cheeks, signaling that he's buried all the way now. Eyes rolling momentarily at the slightly overwheming, _totally_ jaw-dropping fullness they've caused, you sink your hands down into the mattress over Sam's shoulders, pushing yourself up at an angle between the brothers and giving your hips a little experimental roll. 

Three separate gasps fill the room. 

"Oh, Jesus," Dean murmurs, nose squashed against the nape of your neck and lips parting against your skin, breath puffing humid and warm where he's lost control of it. "Something tells me I'm not going to last very fucking long." 

"Same," Sam announces through gritted teeth, his big, splayed hands running up your flanks and moving inward to palm your breasts, the pebbled nipples rubbing against his calloused palms. "This feels too damn good right now." 

You breathe out a sighful moan, practically trembling between as you spread your knees across the mattress as far as they'll go, which jostles their cocks against your inner walls in a way that makes you all groan. "Holy _shit,_ " you whimper, fingers twisting in the comforter either side of Sam's head. "Just fuck me, guys. Promise I don't care how long you last. Just _please._ God, don't hold back on me. I—I need—need you to—" 

"Need us to fuck you nice and hard, huh," Sam supplies below you, trapping his lower lip between his teeth as he smirks. 

" _Yes_ ," you whisper, bracing yourself. 

No other words need to be exchanged. 

Sam and Dean set the pace together. It's urgent, self-indulgent, and _noisy_. It's all skin striking skin, nestled between the thick, wet sounds of their cocks pistoning in and out of you, accompanied by the gorgeous symphony of heavy, pleasure-deep, sex-rasped moans each brothers lets loose without a single _ounce_ of shame. Their hands grope and squeeze greedily at all the parts of you they can reach, fingers digging harshly into your flesh as they fuck the breath right from your lungs, leaving you in a headspace where nothing matters except for them and the way they make you feel. 

It's _perfect._

And just for the record, _none_ of you last very long.

**Notes for the Chapter:**

> Le sigh *chin propped on hand whilst staring off into space dreamily* I would sell my soul for a Winchester Double-Stuff...


	13. Chick Flick Moment ft. Sam LoverBoy Winchester

**Summary for the Chapter:**

> This got a little feel-y ok? Like, it's porn, but also, like, porn with emotions. I mean, the title says it all. Dean Winchester is somewhere cringing, I'm sure. 
> 
> Sue me, bro.

"That's it," Sam whispers, eyes closed in bliss, eagerly accepting the kiss you lean in to give him. "Use me just like that. Fuck yes. Use my cock to make yourself come."

A desperate cry escapes you as you gather what strength you have left, rocking yourself back and forth over Sam where he's hard and blood-hot inside you. Pleasure, warm and honey-like, spills down into your groin, sparks flying from where your clit grinds against the smooth skin just under his belly.

You crack your eyes open, just enough to see the look of euphoria that Sam's wearing. Gone are the hard lines of worry and doubt and self-deprecation that were earlier etched all around his face. He looks calm, regardless of the fact that you're riding him harder than a prized stallion, and he no longer seems to be lost in his head like he had been when you walked into the room—if only for a moment.

You don't want it to end. For yourself, yes, but mostly for Sam.

"Come with me," you whisper back to him, untangling one hand from the sheets to cradle his cheek. The gentle presence of your touch makes him open his eyes, lids dragging up sluggishly until he's looking up at you. It's a look that almost undoes you right then and there. "Please," you say, mouth falling open with a moan, "God, just give it to me, Sam."

"Fuck, baby," he replies, voice as breathy as it is uneven. He raises his arms to wrap them around your middle, using the hold to drag you down over his chest, keeping you there as he uses all that beautiful agility that years of hunting have sharpened to flip you over onto your back.

Once he gets you there, he thrusts his hips in a speed that pulls gaspy little sounds out of you, your body trembling beneath the weight of his as his cock slides over all the right spots inside you. He's the only one who's ever been able to hit them all at once, and with an accuracy that never fails to steal the breath right from your lungs.

You want to wrap your legs around him to get him closer, but you don't, instead spreading them wider to help him get even deeper. The sound he makes against your shoulder when you do makes your cunt throb in response, and it's not long before you feel that urgent need growing between your thighs where you're stretched so beautifully around Sam.

"Oh, my god," you breathe, throwing your hands out to fist at the sheets, body arching up under Sam. "Fuck yes, baby," you moan as you tip your head back, the elongation of your neck drawing Sam in to suck a nasty mark onto your sweat-salted skin as he fucks into you even harder.

The closer you get to release, the looser your filter gets and the less you begin to care about what comes out of your mouth. "Make me take it," you sob in pleasure, bringing your head forward to stare up into Sam's droopy gaze, nodding without reason, "Make me fucking take it."

Sam's face goes slack, his mouth falling open to make way for a loud, guttural moan. He trails his hands along your arms, pries your fingers from the sheets and tangles them with his instead, dragging your interlocked hands up towards the pillows at the head of the bed and holds them there. He rests his forehead on yours, the two slipping against one another from the build up of sweat, and it's such a sweet contrast to the wild way he's bucking between your legs.

"Yes, yes, yes," he hisses when your pussy starts to flutter around him, his hips stuttering just a bit before he pulls it together enough to get himself there with you. "Oh, fuh—" He starts, squeezing his eyes shut and swallowing thickly before spilling forth the most gorgeous sounds you've ever heard from a man. A slick warmth follows closely behind them, one that fills you up then flows back out of you around the hard, velvety pulse of his cock.

The mutual release you share with Sam makes your eyes roll back, hips jerking and legs taking on a shuttery shake as he works you both through it so exquisitely. Through the ecstacy-like haze of it all, it occurs to you that the desperate, pathetic sounds that fill the room are coming from you, and it takes you a second longer to realize that the words Sam keeps chanting against your throat like some sacred mantra are _thank you, thank you, thank you._

It causes your eyes to blur with stinging tears, heart swelling big in your chest at the thought that you're the one who makes him feel this good. That through all the bullshit he's constantly faced with, you're a bright spot for him.

It scares the absolute fuck out of you.

The whispered "I love you," that falls from your mouth before you can even think to stop it is even _more_ jarring.

It's like the air is sucked from the room, making it hard to breathe when Sam slowly lifts his head from the shelter of your neck to look down at you, eyebrows scrunched up in question and lips parted softly where he's panting. You choke back a sob, warm-cheeked and embarrassed by the fact that you're honest-to- _God_ about to cry after sex, and you have half a mind to take back what you said because it honestly feels like you just fucked everything up.

Then, by way of some grand miracle, Sam leans in and nestles his nose alongside yours, lips just barely brushing your mouth. Looking down, you can see the way his jaw flexes, his fingers twitching where they're still intertwined with yours, and your stomach pulls in tight knots when he whispers back, "Not nearly as much as _I_ love _you_."

**Notes for the Chapter:**

> *ugly sobs*


	14. Putting In The Work ft. Reader's Choice

**Summary for the Chapter:**

> Pick your poison, ladies. Dean or Sam?

It was like this sometimes; the built up anticipation of his impending arrival making it nearly impossible to wait. He called to say he was a few hours out and you find yourself thinking up such dirty things that you were slippery between the thighs by the time he got there.

He barely makes it though the door before you're down on your knees, fingers eagerly drawing down the zip of his jeans and hand slipping into his boxers to free his cock. You stroke and lick him to full hardness, which takes no time at all really, then suck him into your mouth and tell him without words how much you've missed him.

He moans your name, tells you how beautiful you are with his cock between your lips, thumbs along your cheek bones as you gaze up into his eyes and bat your lashes for him. You suck him until he tugs at your wrists, wordlessly beckoning you up to your feet so he can lay a greedy, hungry kiss to your swollen lips, hands moving to start ridding you of your clothes until you're overwhelming bare before him.

A sound of approval sounds from deep in his chest when you turn yourself around and bend at the waist, thrusting your ass up into the air as you curl your hands around the rails of the staircase. He takes a moment for himself, admiring the way you so willingly present yourself for his taking, grinning madly as he kicks your feet apart to get a good look at the way your pussy shines with the evidence of just how much you need him.

"We can go slow later," you promise him, breathlessly wanton, sparing a quick glance over your shoulder as he saddles up behind you, one big, long-fingered hand wrapped around the steel-like stiffness of his cock. "Want you to fuck me like I'm _not_ your girlfriend."

With a husked curse, he pushes into you, pulling from you a long, satisfied moan as he stretches you out nice and easy. He sets the pace, gives it to you the way you requested, takes hold of your hips to drag you back into him as he ruts forward. He makes sure to tell you how good you feel wrapped around his cock, how wet your tight little pussy is for him, and how much he thought about you while he was away.

Sweat slicks nearly every inch of each of you before long, your lips parted as cries and gasps of pleasure spill past them. His heavy sac rocks into your clit with every shove in, sparking to life a desperate need between your legs, and just as your about to fall into bliss, cunt flexing in warning, he stills his hips, drawing a high-pitched whine from you at the cruelty of it.

"If you want to cum—" You can _hear_ the smirk. "You're gonna have to work for it."

"H'ohmy _gah_ Ifuckin'hateyou." It's a rushed out response to comes tumbling out of your mouth without much thought, but he knows exactly what you say and gives you a humored little laugh.

"C'mon," he teases, swatting at one round, pert asscheek in a half-hearted slap. "Show me just how bad you want it. Let me see how much you missed having this big cock inside you."

You get to work, inspired by his words, pushing yourself back against him just shy of desperate, working his cock in a way that makes him groan as he looks down to watch the way your pussy takes it. It feels so good, only amplifying when you stretch up on your tippy toes and pivot your hips, finding an angle that has him nudging at just the right spot with every stroke.

He feels you pulse around him. "Hell yeah," he breathes, giving you a heavy-handed slap that makes you jerk and choke on a moan that gets stuck in your throat. The prickle of pain sets you alight, makes your movement more erratic and less coordinated, but you get yourself there, white bursting behind your lids when you squeeze your eyes shut and shout your release.

" _That's_ my girl, yeah. That's a _good_ fucking girl," he keeps saying, hands skirting up your naked back until he's curling them around your shoulders, using it as leverage as he begins to fuck into you roughly. _Fuck._ You haven't even had time to catch your breath, your weeping pussy still fluttering around his rock hard cock. "That's right, baby," he growls in pleasure, tangling a hand in your hair and twisting, making your scalp sing when he tugs your head back. "Take my fucking cock just like that. Take every inch inside that sweet little cunt of yours."

You fold like a house of cards with every word that leaves his filthy mouth, body feeling as if it's close to implosion as he pounds you towards a quickly-approaching second orgasm. He's so _deep_. No one has _ever_ filled you up like he does. You could cry tears of pure happiness at all the pleasure he's giving you.

__

With a loud sob of his name, you cum again, knees nearly buckling under the intensity of it all. He's there, though, wrapping his strong arms around you; one banded around your waist and the other criss-crossed across your chest, holding you so intimately close as you tremble against him. He kisses at various parts he can reach, whispers praises and words of adoration into your ear, gets a hand down between your thighs to gently rub at your neglected clit to draw out your release as long as possible—all while rocking his hips into your ass where it's cradled against him.

__

You've only just come down from the high when he tells you, "Gonna make you cum until you can't possibly cum anymore. Not gonna stop 'til you're begging me for mercy."

__

You sigh, dazed but up to the challenge, responding with a playful, "We'll see about that."

__

He hums a laugh, grins at your moxie. "Yes, we most certainly will."

__

**Notes for the Chapter:**

> Tell me which brother you thought of ;) I'm ~~nosy~~ curious.
> 
> &lolz, y'all like how I switched things up and used 'cum' instead of 'come'? Felt a little weird at first but I kinda like it *shrugs*


	15. Best Mistake ft. Dean

**Summary for the Chapter:**

> Alright. I'mma be honest and tell you guys that I'm a little high right now. (Lil weed never hurt no body) I was watching porn bc obvs... anyway I stumbled across this video and immediately thought of Dean. I wrote this in like thirty mins (idk could've been three hours, but like I said I'm high af) so sorry for any grammar mistakes and if it sucks and you think I should never write while under the influence of the marijuana, just lie to me ok??? Love you 🖤
> 
> Edit from sober me: lmao I'm actually impressed by this. I thought for sure when I came back to re-read this that I was going to be hella embarrassed but... it ain't that bad I guess. And high me is a freak - the "shoot his load down into your belly" line - yeesh. Who am I? Who do I think I am? 😂

It all started when you couldn't find any hose in your overstuffed duffle. You'd left all your pairs back at the bunker which by then would've taken days of driving to get back to, and with the case you were working, completely turning around would have been a massive waste of time. Not to mention, stupid and pointless to boot.

So, you stopped at the first Walmart you came across, praying that they had something decent enough to wear with your fed suit. Dean had opted to stay in the car, citing that he'd just be deadweight following you around and that you probably didn't _really_ need him staring over your shoulder when you sifted through the delicates section of the store.

Turns out, you found some that seemed okay, good enough to get you through the hunt at least. Then, just as you were moving to get yourself to a self check-out, you saw them—black fishnet stockings. They were the cheap kind, the brand that wasn't known for holding up too well over long periods of time, but with the ideas you had in mind, they wouldn't really be needed for too long. Nope, in the deep, dirty recesses of your head, they would only serve one purpose and one purpose only before they met their end.

You bought them.

You waited until the case was finished, controlling yourself just enough to keep your focus where it needed to be, and waited for the right time to whip out those fishnets to initiate your evil little plan. Fun, _sexy_ plan, of course, but utterly sinful at the same time.

The opportunity presented itself the last night you'd be in town, shacked up in some cheap motel room that had sucky TV channels but decent enough sheets. Dean had gone to take a shower before bed, and while he was in the bathroom, you flitted around the room, excitement simmering underneath your skin as you got yourself ready to surprise Dean.

He came out of the bathroom, smoke billowing out behind him, just in time for you to seat yourself at the foot of the bed with one knee crossed over the other and not wearing much. Just those fishnets and a black, strapless, bandeau style bra.

Dean froze when he saw you, his deep, mossy eyes widening to that of a deer caught in the high beams. It made you giggle, trapping your plump bottom lip between your teeth and letting it slide through them until it snapped back into place.

"You gonna stand there all night gaping like a fish on land," you pondered, slowly pulling your knees open so he could see your bare cunt through the fense-diamond stockings. "Or are you gonna get over here and fuck me, Winchester?"

Dean sprung into action, immediately taking control and demanding you get up on the bed on hands and knees. You obeyed without hesitation, sticking your ass up in the air and shaking it for him as you waited for him to join you. When he did, he wasted no time sliding two fingers through the hole that laid against your pussy, sinking the thickness of them into the wet heat of you. He drew sweet moans from you, your tone high in pitch and frequent in occurence.

Then, just as you were about to start cumming, Dean pulled his fingers out and gave your ass a heavy, stinging slap, causing you to gasp sharply. He didn't give you a second to breathe before he was tangling his fingers in the cheap mesh between your legs to easily tear a hole big enough to free your pussy, leaving no obstruction to get in his touch's way.

You practically begged him to continue what he started, but Dean had had other ideas and let you know in certain terms that he wanted you to suck his cock. You had not a single qualm or complaint, mouth suddenly watering at the idea of feeling that velvety-smooth stiffness slide between your lips, over your tongue, and down your fucking throat.

Dean situated himself standing at the foot of the bed, guiding your mouth to him when you eagerly got yourself into position and leaned in to take him. A deep moan rattled up from deep in his chest when you dropped your jaw and invited him in by sticking out your tongue, your stretched lips curling with a slinky little smile when he slid in the spongy crown of his cock. He teased himself over the tiny ridges of your tastebuds, sinking more inches into your willing mouth when your eyes flicked up to meet his where they were casted down to watch you.

When you tightened your lips to start sucking him, Dean dropped his hands at his sides and let you take the lead. _Great fuck._ You loved sucking his cock, loved even more the idea that it was _you_ making him feel good. It never failed to turn you on more and more with every suck, lick, swirl, and your personal favorite, choking gag.

Mid blow-job, you realized how _empty_ your pussy felt, painfully aware of how wet you were getting just by having Dean in your mouth. Deciding you needed to try and tame the wild throb running rampant between your legs, you reached back and sunk a few fingers into yourself, looked up into Dean's eyes as you started fucking the digits in and out, hips rocking at the small tinges of pleasure that zinged up through you as a result.

"Fuck," Dean cursed under his breath, eyes tracking your movement. "You're so fucking sexy, sweetheart," he told you, raising his arms to slide his fingers through his cropped hair on the sides of his head, eyes fluttering in bliss as he took a moment to enjoy the sweet suction a little longer before reaching down to cup your jaw and the back your neck. "Wanna fuck that hot little mouth of yours," he breathed, staring up a nice rhythm that made your lips go a little numb as he passed between them, "Wanna feel that tight throat choking on my thick cock, baby."

You hummed your approval, eager as you nodded, pussy pulsing hungrily around your fingers when he started fucking your mouth. And you knew for a fact, that you're going to cum soon and that you wanted Dean shooting his load down into your belly when you did. He knew it, too, able to easily pick up on the vibe.

Then and there, you knew accidentally forgetting your hosiery at the bunker was the best mistake you had ever made.


	16. Close Call ft. Sam

" _Shit_ ," Sam hisses above you, his narrow hips stuttering to a halt between your spread thighs.

"Huh?" You respond dumbly, dazed by the pleasure that's been suddenly put to a stop, whining in protest when Sam pulls all the way out of you. "No, no, no," you pout, curling your hands around his shoulders to tug weakly, "Come back."

"Stop," Sam chuckles, leaning in to press him face into your neck, lips smearing across your skin. "Not goin' anywhere anytime soon. I just...give me a sec, 'kay?"

The cogs in your head finally start to turn. "Ohhhh," you grin, wrapping your arms around his shoulders, letting a giggle flutter past your lips. "I didn't realize—"

"Shut _up,_ " Sam huffs, pulling his head back up to smile down at you, playfully rolling his eyes. "You just feel so _fucking_ good," he tells you, swooping down to capture your lips in a soft tug, hands ghosting up your ribs, "Nearly forgot how wet you get, or how you tighten up when I hit just the right spot."

"Yeah?" You breathe, cradling his jaw in your hands, the five-o'-clock shadow rasping against your palms as you look up into his hooded, desire-dark eyes. "Well, you kinda do it for me, Winchester. That hot ass of yours never fails to get me all worked up."

Sam's responding grin is big and dimpled, making your heart swoon. "S'been too long since we did this," he whispers, giving you another saccherine sweet kiss before hooking his hands behind your knees, easily spreading you open and holding you there as he crawls backwards. "Also been too long since I've had my mouth on this pretty little cunt," he grins hungrily from between your legs, dropping his head to drag his tongue through your dewy folds.

A low moan spills out of you, brows tilting with the pleasure. "You were literally _just_ down there, like, less than twenty minutes ago," you remind him, pussy clenching around nothing when his eyes snap up to meet yours as he presses the flat of his tongue against your clit, giving you a languid lick that's heavy and wet and so marvelous it should be illegal.

"Like I said," he sighs, lips tickling against yours, breath moist and warm on your tender flesh, "Too fuckin' long."

Sam goes back to work and you watch him, belly warming almost overwhelming hot at the sight of his face between your thighs. He's got his eyes closed—he'd let them flutter shut the moment his mouth was back on your clit—and it's like he's enjoying his favorite meal with the noises he keeps making as he eats you.

It's not long at all before—"oh, God, Sam. You're gonna make me come."

He nods, just a small acknowledgement while he's lost in you that says _yes, do it, come for me_ , and boy, do you ever.

Bliss swallows you up and leaves you drowning, your world narrowing down to the place where Sam's curling his tongue into your pussy as it uncontrollably flexes, these hungry, ravenous sounds rumbling through him as he covers nearly your whole sex with his mouth and drinks you down like a glass of fresh lemonade on a hot, sun-bright day.

"Fuck, baby," you pant, letting your head lull back as he sucks at the pulse of you, gasping sharply when he pops free and climbs back over your trembling form.

With one swift, purposeful movement, Sam got his cock buried inside you once again, hands splaying out in the spaces on either side of your head in order to gain the leverage he needs to snap his hips back and forth the way he wants. The sheer skill and rhythm he sets steals the very breath from your lungs, pulling these broken, raspy, high-pitched cries from your lips as the most gorgeous man you've ever met—both physically _and_ otherwise—fucks you better than anyone else ever could or even attempt to.

"This fucking feels too good to be real right now," he snarls in pleasure above you, hiking one of your knees up until it's sitting high up on his ribs, allowing him to hit at you in a better, more mind-numbing angle.

"Uh-huh," you nod weakly, too focused on the way his cock is stretching you open to even try and string together a full, intelligible sentence. You curl your hands around his biceps for some sort of anchor, hips flexing beneath him as pleasure, white-hot and quickly building, spreads through you like wildfire. "Sam, I—oh, my _goodness_ —I'm about to— _huh_."

"Me, too," he tells you through labored breathing, dropping himself down enough to press his forehead against yours. " _Fuck._ I'm right there with you, beautiful."

He doesn't stop until you're both shaking.

* * *

After a not-so-surprising third round, Sam's crowded up behind you, acting as the big spoon as he brushes his fingertips up your arm and down your side over and over again.

"You should move into the bunker," he says out of no where, voice quiet and maybe a bit unsure.

Your heart picks up speed, now fully awake from the slumber you were slowly but surely slipping into.

"It's not enough to only see you a handful of times a year," he explains, lips ghosting along the shell of your ear. It feels so intimate that your belly whooses inside you. "I'm not asking for any type of committment or a relationship that goes beyond what we already have, if that's what you're thinking. We both know neither of those go very far in this life we live," he clarifies, "I just think it'd be good for you to put down some roots somewhere, ya know. A place to call home when you need it, when the motels and open road get too lonely—because I know they do."

You smile. "Is that your way of asking me if I want to be your personal in-home booty call?"

Sam gasps, playing shocked, the laugh that follows soft and humored in your ear. "You caught me," he teases, smoothing a hand down your belly until his fingertips just barely graze over the soft mound between your legs. "It would _also_ be nice to fuck you when I want," he confesses in a heated whisper, fingers slipping between your sensitive folds, sweeping over the swell of your clit so feather-light that you shiver against him. "This whole playing phone tag to pin you down and set up a time to meet just isn't cutting it anymore."

With a sigh, you turn your head and giggle lightly when Sam nuzzles his nose into your cheek. "Let's assume that I agree. _Hypothetically_ ," you tell him, lifting a leg and hooking it back over his to open yourself up to his wandering caress. "Would Dean even be okay with me staying there? It's his home as much as it is yours."

"Let _me_ worry about Dean," Sam assures you, dipping two fleeting fingertips into you before gliding back up to drag circles around your now throbbing little bundle. "If he gets his panties into a twist about it—well, I'm a big boy; I can share," Sam husks, making you gasp in surprise, "There's no doubt in my mind that he wouldn't be able to blame me for wanting you around if he were to get a taste for himself."

"You naughty man," you grin, reaching down to guide his hand father back, encouraging him to sink some fingers into you, "Talking about letting your brother have his way with me. I mean, I _have_ always found Dean to be a rather handsome man."

Sam hums, tickled. "I'm smarter and bigger in the ways that count," he reminds you, crooking the digits inside you so he brushes along that sweet spot, "Trust me, I've shared quarters with the guy nearly my whole life—I'd know."

You giggle playfully, the sound cut short by a soft moan. "Well, you've made the offer. Now prove to me why saying yes would be the right answer."

Sam does just that, sucking gently at the pulse point just under your jaw as he fingers your pussy like it's all he's ever wanted to do. And as if he hasn't taken you by surprise enough for one night already, when he's got you right up on the cusp of another fantastic orgasm, he murmurs in your ear, "I haven't been with anyone else since we started sleeping together. Just thought I'd throw that out there just in case that were to help sway your decision into the more agreeable territory."

It's been years since you starting having sex with Sam. _Years._ Now he's telling you that you're the only one he's slept with this whole time?

You believe him right away, and it occurs to you that it would shock you to your utter core if you weren't in the same boat.

"My, my," you gasp, rocking your hips down into his working hand, "That sounds an awful lot like commitment to me, Sam Winchester."

He chuckles. "What can I say? I'm a bit of a hopeless romantic," he tells you, quickening his fingers, "Now come for me so I can slide up inside you and solidify that yes you're just _dying_ to say."

"My pleasure."

"Yes, it absolutely will be."

**Notes for the Chapter:**

> Just imagine having a pu$$y so good that Sam Winchester has to stop himself from cUmMiNg too soon... _HELLA SIGH_


	17. My Own Little World ft. Sam

**Summary for the Chapter:**

> did y'all miss me? I've been distracted (by Sam and Dean, sure, but work and life mostly), but here's the next installment ;)

_"You take me so well," he whispers in your ear as he curls a strong hand around your throat, your messy tresses tangling with his long fingers. "That wet little pussy feels so perfect wrapped around my hard cock, baby."_

_"Sam," you whine in pleasure, reaching back to sink a hand of your own into his hair, the silken locks slipping so smoothly through the spaces between your fingers. "Fuck me harder," you request, gasping, "Please."_

_He might be the one in control, but Sam can never deny you, especially when you ask so nicely. He gives in without question, quickening his pace significantly, the sharp, repetitive sound of his hips striking your ass with every thrust like a song you want to put on repeat all day._

_"There!" You cry when he hits the mark, "Oh, God, Sam! Don't stop—fuck. Keep fucking me just like that, baby."_

_"You gonna come for me again?" He questions in a deep, rumbling husk, the hand on your neck moving down to pinch tightly at one of your pebbled nipples. "Huh? Gonna soak my cock some more?" He smirks as your hips twist in response to the painful pleasure his skilled fingers are causing._

_"Yes!" You answer, your proceeding mean high-pitched and desperate as the needy feeling between your thighs grows and grows. "'m gonna come all over that big, beautiful cock, Sam," you tell him, breathless and shamelessly sluttish when you reach down to rub rhythmically at your throbbing clit, pulling from yourself a pathetic whimper at the way it accelerates the process. "I'm gonna come so fucking hard for you, baby."_

_"Gimme everything you got, baby girl," he growls in your ear, hips snapping just a bit harsher now, "I plan on making you come over and over again, until that sweet, tight cunt can't possibly take anymore."_

_His words, the lyrics to the song of his thundering hips, sparks a spreading warmth that starts somewhere deep inside you and fans out until you can feel it all over. Powerful, wave-like pleasure pulses through you, causing musical sounds to spill from your open mouth that mix with the whispered encouragement that Sam harmonizes in your ear._

_"That's it, beautiful, yes," he breathes, still fucking into the grasping clutch of your sopping pussy, working you to higher and higher heights of release. "Fuck, that feels good," he tells you, rewarding you with a sharp, echoing slap to your bare ass that makes your eyes cross in your skull, "That hungry pussy squeezes me so goddamn perfectly every single time."_

_You hum in response, looking back over your shoulder and searching for his mouth. He meets you halfway, lips sliding over yours in a hot, panting kiss, his hips slowing to a gentle rock._

_"Want you to clean me up," he tells you, tenderly thumbing over the swell of your cheek. "Want you to get down on those pretty knees for me and get me nice and ready before I sit you on my cock."_

_"Yes, sir," you nod, playfully tugging at his bottom lip with your teeth before pulling away from him and dropping gracefully to the floor at his feet. His cock, still hard as rock and glistening with the creamy evidence of your end, bobs so enticingly between his strong thighs. You look up into his downcast eyes as you lean in and twirl your tongue around the tip, keening at the taste of yourself on him._

_"Take me in your mouth, baby," he husks, pushing hair out of your face and tucking it behind your ear. "Suck me."_

_You obey without hesitation, sealing your lips around him and sinking a few inches over your tongue, closing your eyes at the unique and familiar tang that coats them. You suckle at him for a short moment before popping off to say, "My pussy taste so good on you, Sam."_

_He grins down at you. "I can imagine," he says, hooking his thumb into your mouth and behind your teeth to lower your jaw to push his cock back inside, "You're my favorite flavor."_

_Your cunt throbs in response and you eagerly let him fuck your—_

"Yo!" A loud voice bleeds in, "Earth to Y/N!"

"Shit," you gasp under your breath, jumping in your seat as reality comes crashing down around you and finds you in the bunker library room, where you've been stationed for hours now. Your wide eyes look at Dean, who's looking a you with confusion, and then you look to Sam, the pounding between your legs obnoxiously incessant as you meet his concerned gaze.

"You good?" Dean questions, making your eyes snap back to him, your mouth open but suddenly unable to form words. "You were staring so far into space, I don't even think you were in the same galaxy anymore."

Your tongue feels thick in your mouth when you try to speak. You don't dare look at Sam again, the warmth that fills your face when you do almost too unbearable to handle.

"I, uh...c-coffee," you finally say in a pathetic rasp, giving your head a shake to try and clear it, "I...I need coffee."

You stand from your chair, ready to disappear for a few hours to try and relieve that ache that's growing bigger and bigger in your belly with every passing second.

The boys watch you leave.

"Did she seem..." Sam starts, waving his hand in a motion that Dean's meant to decipher.

The elder brother snorts, reading the younger easily. "Hornier than hell? Ch'yeah." He smirks. "Which one of us do you think she was daydreamin' about?"

Sam rolls his eyes. "Who's to say it was _either_ of us?"

"With the way she got all twitchy and stuttery," Dean chuckles, "It was definitely me or you."

Sam shrugs, looks down at the big, open tome in front of him, and tries to not get jealous over the fact that it's a fifty-fifty chance you were thinking about his brother.

"Let's just get back to our research, Dean."

Sam also tries—and _fails miserably_ —not to think about why you don't come back in the time it takes to brew a pot of coffee, losing himself in a world of his own for a while. One where you're naked and spread out on a bed—yours or his, he doesn't really care—with a hand between your legs and his name on your pretty lips.

Yeah. He fails with flying colors.


	18. Connection ft. Dean

**Summary for the Chapter:**

> I gave you Sam, now have a little Dean 😘

Dean knew he was done for the second his sunk his cock deep inside you for the first time. 

Your lids fluttered in pleasure as he buried himself to the root and worked up a slow, steady rhythm, your hands reaching up to cradle his face as you held his gaze. Whispered praises fell your open mouth, nothing too loud or over the top, just soft words spoken into the short distance between your lips and his, noses and foreheads nuzzled together so closely. 

It took Dean all of five seconds to realize that this was so much more than just fucking or even making love. This was _connecting._ It was being so close, so open and willingly vulnerable with one another, that it made the outside world fade away into the background, bringing to the forefront nothing but want and need and desire. It was getting so lost in the good feelings, that the bad ones didn't matter in that moment—maybe they never had. 

For a few short, intimate moments, all that mattered is how you felt all around him. All he had the mental space for was how wet you were around his impossibly hard cock, or how beautiful you sounded when you moaned or spoke his name in true bliss. All he cared about—his only mission right then—was getting you there over and over again until he'd exhausted himself. 

Dean realized half way through that he'd never wanted anyone more than he wanted you. Years of friendship and trust-building had led to this very moment, a moment so monumental that Dean wondered why he waited so fucking long to have this with you or why he wasted so much time seeking this in other women. 

His fate felt sealed; you were his and he was yours. Truly and unarguably. 

"You feel so good, Dean," you told him, fingers slipping through his cropped hair as a whimper worked it way up your throat. "So much better than I could have ever imagined." 

"You, too, sweetheart," Dean whispered back, his heavy-lidded eyes still locked with yours. "You, too. _Fuck_. C'mere." He leaned in, closing the gap, and kissed you soundly, just pouring himself into a kiss that made him feel a little dizzy when he eventually pulled back to let you breathe again. 

"I wanna come together," you requested through your panting against his lips, curling a soft hand around the nape of his neck as the other glided down his flank, farther and farther until you were gently tugging at his ass where it flexed with each thrust. You sounded so wrecked, but so unashamed and wanton for him, too. "Come inside me, Dean, please. I...I want to feel you, baby." 

Dean shivered against you, groaning openly at your words. "Anything you want," he managed, sinking a hand into your hair and letting his fingers get all tangled up in it, using the hold to keep your mouth tilted up against his as his hips quickened in their pace. "I'll give you whatever you want, pretty girl."

You cried out in pleasure, fingernails digging into his flesh, thighs quaking where they lay open for him. "Give it to me," you murmured as your pussy pulsed in warning around him, "I want all of it, Dean. Fill me up, baby." 

Dean gave it to you without a moment's hesitation—his heart, tattered and stapled together at this point, included.

**Notes for the Chapter:**

> Oh, you thought I'd forgotten about the porn with feels? Think again. I'm a dirty tramp with emotions 😭


	19. Anything But Boring ft. AU!High-Society!Promising-Law-Student!Sam

**Summary for the Chapter:**

> **AU** \- The reader and Sam come from two of the country's richest families, and both harbor a great dislike for snobby, show-off affairs.
> 
> A Romeo + Juliet type, but instead of family war and death, there's champagne and fucking and lots of gratuitous, disgusting dirty talk. (So for my readers who ain't into too much talking during the sex - I'm so very sorry for this...)
> 
> P.S. I put the porn gif into the actual part of this chapter where it belongs. Just think of it as a nasty little surprise ;)
> 
> P.S.S. this damn thing is 4k+ words long lmao self control? Who needs it?
> 
> Update: I'm not sure what happened to the gif and I can't find it anywhere, but here's the link to [the video it came from.](https://www.peekvids.com/v/method-actor-abella-danger-jean-val-jean-fuck-me-videos-prettydirty/AA7oRSp3XUd) The inspiration came from the 22:04 mark. Warning!! This is a porn flick so maybe don't watch this around family lmao

**__ **

**_T_** here were some downfalls to being a member of one of the richest families in the country—one being the fact that you were forced to waste yet another Friday night showing face at yet _another_ boring, laughably lackluster soiree hosted by your no-expense-spared father. 

It was all so suffocating; milling about the same room all evening, speaking to the same dull people from the last event, the ones who spoke so far above your head about shit you couldn't care less about if you tried your damndest. It typically led to you drinking yourself silly, swiping flute after flute of expensive champagne that made its constant rounds around the ballroom on sterling silver platters. This at least dulled your senses enough to make it through the night with a doped up grin on your face, bringing to the forefront your learned skill of faking it 'til ya make it for your father's reputation's sake.

Tonight, however, there was something far more appetizing than drunken acting in your sights. 

It was a man—mid twenties like you maybe, tall as all hell, gratuitously attractive in a well-fitted tuxedo, and built like a fucking marble statue put on display to make all the male-attracted persons swoon helplessly. The one thing that made you take a second look—and a third and a fourth—was the fact that he seemed just as bored out of his skull as you'd been, standing in a small group of other sharply dressed men, hands shoved in his pockets and mindlessly nodding along to whatever conversation was happening around him. 

You'd witnessed more than a few times him throwing back champagne like it was water, this comical, pensive look of disinterest unmoving on his handsome face. The only time you saw it dissolve just a bit was when he eventually caught you eyeing him from across the fancy ballroom. 

This little smirk curled up on his slightly-parted, candy-pink lips after he met your gaze, drawing out just the barest hint of a dimple that made your belly fill with swirling warmth. His tongue moved along his teeth like his appetite had just spiked and when he nodded his head to the right just a bit, as if to silently invite you to something, you coyly sank your teeth into your bottom lip and nodded back in the direction of a long, deserted hallway. 

Without waiting for his reaction, you turned towards it and began the trek down the hall, letting your hips sway just a bit looser as your heels clicked along the freshly polished marble flooring. At the end you find a small room like a study, thankful for the unlocked door. It was darkly lit, various antique-y lamps strewn about that cast the space in a warm yellow hue. 

You left the door open as you waltzed inside, heart kicking up in your chest when you heard it click shut not even a full minute later, quickly followed by the mechanical song of the lock being flicked secure. You moved to stand just a few feet away from a brown-lather, Chesterfield-style sofa that sat in the center of the room, pondering for just a second what kind of sounds it must make if two people were to fuck on it. 

The soft footfalls on the carpet behind you made you chew at your bottom lip in anticipation, a little hum of greeting vibrating in your throat when they ceased and the heat of someone standing behind you melted into your skin. A hand, sure and slow, rose to move the hair off one of your shoulders and over to the other, followed by a set of hot, curious lips on the now accessible pulse-point just under your jaw. The gentle cling of a kiss there quickly morphed into a wet sucking that made you gasp and clench your thighs together, releasing a soft sound when you felt yourself begin to gently throb between them. The man behind you, a complete stranger, wrapped his grip around your waist, tugging you back against the solidness of his body, pressing himself into you and groaning such a deep, sexy sound into the flesh he'd been laving with attention. 

You rocked your ass back into him, tipping onto the toes of your heels to gain just a bit more height so you could rub yourself against the crotch of his tux pants. A wanton moan fell from your slack lips when you felt his confined cock begin to stir and harden, your mind taking a mental note of how he felt hung as fuck even through clothes. 

When the need to see him started to overwhelm your senses, you turned yourself around in his hold and looked up into his eyes, losing yourself in the intensity of lust-bright hazel. His gaze dropped to your mouth and he leaned in at the same time you did, until his lips crashed into yours in a meeting of teeth and tongue, the dominance of him loud and evident in the way he claimed you with the filthy kiss. His big hands roamed down the sides of you until he was moving in to palm your ass and squeeze greedily, using the grip to drag you up against him further, his now fully-erect cock pressed against your lower belly. 

You anchored yourself to him, letting him drive the thing as you sunk your hands into the silk of his hair and melted like butter in his strong arms. A squeal of surprise jumped from your lips when he suddenly and in quick succession reached down, hooked his hands around the backs of your thighs and hosited you up as if you weighed nothing more than a sack of feathers. You giggled into his mouth, wrapping yourself around him as he dropped down to the sofa, the leather creaking as he settled himself overtop you. 

"Hi," he greeted in a low husk, his grinning mouth just barely brushing yours as he gazed hungrily into your eyes. "I'm Sam. Sam Winchester." 

"Y/N," you grinned back in a breathy, desire-drenched tone, letting your hands fall beside your head and pitching your hips up against his as you add, "Y/N Carmichael." 

His grin fell to a smirk of recognition. "Carmicheal, you say? As in Harold Carmicheal, who I assume is your father." 

You trapped your lower lip between your teeth and nodded slowly, sighing dreamily when he gently rocked into the space between your thighs, the heat of him meeting the heat of your bare cunt. 

"My father is currently trying to schmooze yours, apparently," Sam chuckled, leaning in to get his mouth on your neck, his teeth worrying at your flesh in tiny nips that made your breathing grow high and needy. "I've been told they're actually enemies of some kind," he further explained into the dip in your throat, which he filled with his wet, hot tongue mere seconds later, "Now sure why. I'm sure it has to do with the fact that they're two of the wealthiest men in America vying to see who can out-rich the other." 

"What a pity," you purred, reaching between your bodies to get a hand on his cock and gently squeeze the steely length through his slacks, enjoying the way his mouth went slack and how his brows tilted. "I suppose they'd have reason to despise each other even more if they knew their offspring were fondling each other just a few yards away from their great, big, fancy, _boring_ party." 

A dark look pooled in Sam's eyes. "By fondling, I hope you mean fondling-turned- _fucking_ ," he husks, rocking himself into your perfect grip on him. 

You giggled lightly. "Oh, absolutely." 

He hummed in response, reaching down to get his own hand between your thighs. A look of joyous rapture filled his face when his fingers met the dewy seam of your pussy, the roughed pads of his fingertips sliding through through the lips to assess how slick you were. 

"What a naughty girl you must be," he grinned in filthy delight, easily sinking one long finger inside you, quickly followed up with a second which stoked the building heat in your core. "Do you always walk around formal events without panties on?" He asked in that low, honey-smooth voice of his, leaning in to drink down your needy little sounds with greedy lips. "Does the risk of some stuffy business man seeing up your tiny dress get this sweet little pussy of yours all hot and wet?" 

You tipped your head back and moaned through a laugh, spreading your legs wider to give him more space to work. "I know one man in particular who is getting me all hot and wet right now," you answered, bringing your gaze back to his and reaching down to pluck open the buttons of his tuxedo jacket and yank the tails of his shirt from where they were tucked into his pants. "I want you to fuck me," you told him, working loose the buttons of his dress shirt just enough to see what's hidden beneath, breathing a dreamy breath when you traced your fingers over the rippled flesh of his strong chest and torso. "I want you to shove this big, hard cock—" you sank a hand lower to squeeze at him once again, smiling at his responding growl, "—inside my wet, _willing_ little pussy." 

Sam reacted bodily to your words, hastily reaching down between the two of you to unthread his belt and undo his pants, the symphony of metal clinking and grinding making you moan and your pussy clench excitedly around nothing. You casted your gaze downward as Sam pushed at his clothes, watching as he lowered them just enough to free his cock so it swung free and heavy and blood-flushed between his legs. The pearly bead of precum weeping from the tip made your mouth water for a taste. 

"Fuck, yes," you breathed, moaning as Sam wrapped a hand around the shaft to give himself a few attentive, preparatory strokes. Your gaze flitted up to once again meet him where he was watching your expressions. "I fucking want it," you exclaimed, drawing your knees towards your chest and out as you hiked up the hem of your short, fancy party dress, opening yourself up to the man who was still practically a stranger. "Give it me, Sam," you pleaded shamelessly, feeling resolutely desperate, "Make me take every inch of that beautiful cock. Wanna feel you stretch out my tight fucking pussy, baby."

"Shit," Sam cursed under his breath, looking down as he notched the head of his cock at the slick dent of you. "Keep talking, beautiful," he requested as he began to push into you, all thick, rock-hard and blood-hot, "Wanna hear all the nasty little things you keep in that pretty head of yours." 

"Oh, _fuck_ , Sam" you cried out as he sank deeper and deeper and _deeper_. "Fuck me. Oh, God, please. Fucking take me." 

Sam pressed his hands into the sofa on either side of your head, fingers splaying wide and gripping at the squeaky leather as he started up a heavy, pounding rhythm that made stars burst in your vision where your eyes crossed back into your skull. It was perfection personified, the way he fucked into you like you'd only ever dreamed of before, lost in pleasure that was without any restraint. 

"So fucking good," he growled, squeezing a hand under you to blindly search for and eagerly drag down the zip of your dress, "You feel so good wrapped around my cock, baby. So wet for me, clenching so goddamn tight." 

You sobbed in response, the pleasure of him filling you up so full and fast making it hard to do anything else. Using arms that felt like rubber, you clumsily yanked your dress up your body and off, leaving you completely bare beneath Sam except for your heels. His eyes went bright at the sight of your swaying breasts, his lips going slack as he leaned down to take a peaked nipple into his mouth and suck greedily. You gasped and sank your hands into his hair, squashing him to your chest and reveling in the way the stubble on his chin and cheeks rasped along your skin. 

"I wanna come for you," you told him breathlessly, feeling drunk off the way his cock slid so exquisitely over just the right spots. "I'm—oh, shit, Sam—I'm so fucking close." 

You could feel that desperate need growing in your groin, molten-like heat licking at your insides as Sam shoved you closer and closer to that blessed edge. But, as if to almost be cruel, Sam breathed out heavily and pulled himself from your body, making you cry out with the loss of the fullness he'd provided. 

"Turn around," he commanded, a sweet bite of dominance laced throughout his words. "Hands and knees, gorgeous. I want to see that ass up in the air for me," he explained, "Show me how bad you want it." 

You obeyed and moved to flip over, albeit a bit slower than he liked thanks to the fact that your legs and arms felt like jelly, useless and heavy. Sam helped, or rather _manhandled_ you into his preferred position, hands bossy and impatient in their grip. It made you mewl in delight, a grin stretching your lips over your teeth as he pushed and shoved and tugged at you like you were a toy meant for nothing more than his play. He wrapped a hand around the back of your neck, keeping your cheek pressed to the leather beneath you as he used the other to pull at your waist, encouraging you to rise up high on your knees and curve your back so your ass was where he deemed acceptable. 

"That's a good girl," he praised, his lust-dark eyes taking in and appreciating your form. "So damn sexy like this, all wet and willing and desperate to come for me." 

"Yeah," you agreed, swinging your hips left to right in a sensual invitation, which Sam accepted by sinking his cock back into you, the fit so much more snug this way. "Oh, my god," you gasped, grappling to get your hands on the arm of the sofa to ground yourself. 

"Jesus," Sam spat through clenched teeth, snapping his hips back and forth to work his hard, throbbing cock into the clutching heat between your legs. "Such a perfect fucking pussy, baby." 

Sam finished his filthy praise with an earnest slap to your ass, making you keen and beg, "More, Sam, please. Spank me again. _Harder_." 

Sam made an approving sound, wrapping his free hand around the front of your throat and dragging your upper half up, pulling back so your spine was beautifully arched.

[*missing gif - see beginning note] 

"You like being spanked, huh?" He questioned, hand splayed out on one round, supple cheek, fingertips dimpling the flesh. Two stinging strikes followed, making your mouth fall open in bliss, your labored breathing coming out in soft, raspy bursts as Sam tightened the hold he had around your throat. "You love it, don't you?" He spoke against your forehead where he had your head tilted back towards him, "You love having your tight little cunt used like this. Fucking love being treated like a dirty slut, don't you, baby." 

"Yes!" You cried out in a ragged moan, so on fire for the man behind you that it felt almost overwhelming. He seemed to know you better than any man before him, checking so many of the boxes on your imaginary _requirements of a good and thorough fuck_ list on his first go. "I love it, I love it, I love it." 

"Such a good girl," he grunted into your hairline, hips still moving in a relentlessly perfect rhythm. "Dirty, _dirty_ good girl," he breathed, "Gonna make me fucking come like this. You gonna come with me? Gonna squeeze and milk my big, hard cock and let me fill this sweet cunt up?" 

"Yes, yes, yes," you gasped, so far gone, "Gonna come, gonna fucking come." White speckled and faded in your vision, fat, rolling throbs of heat whooshing inside you. All your world narrowed down to nothing but the pulse of Sam's cock in and out of your pussy and the thick, wet sounds that accompanied it. "Don't stop, don't stop—please, Sam, _please_ don't fucking stop." 

Sam's moaning met your ears and the blissed out sound of it made you tighten around his cock in warning. "Yes, baby, that's it. I can feel it— _fuck._ Come with me, dirty girl," he rasped, hips working more erratically, "Come all over my fucking cock." 

The first wave of your release was an onslaught of sensation that made your eyes grow glassy and wet, leaving you breathless and shaky. Sam, lost in the throws of his own completion, rutted into the quivering, rippling grasp of your slick cunt as he heaved such heavy, commit-to-memeory sounds, all of it working to extend the life and intensity of what was shaking up to be the best orgasm of your entire fucking existence. This was only made more overwhelming when Sam landed a series of heavy slaps to your ass then reached around to get that same hand between your legs, his long, adventurous fingers rubbing expertly at your neglected-but-silly-sensitive clit. 

You must have blacked out for a second, because the next thing you remembered was Sam showering your sweat-glistened back with sweet, sucking kisses as you lay boneless on your belly beneath him. He was murmuring more praise into your skin, his words seeping down into somewhere deep inside you. 

"Holy shit," you whispered once your brain started working again, lazily rolling under Sam until you were on your back, looking up at him with slitted, come-drunk eyes. "The son of my family's sworn enemy," you teased with a small grin, trailing your fingertips down the angles and lines of his handsome face, "The best fuck in all the land." 

Sam's chest rumbled with deep laughter, his responding smile all dimpled and rosy-cheeked. He dropped his head and captured your lips in a slow, surprisingly sweet kiss. "The daughter of family's sworn enemy," he husked against your mouth, his finger sweeping some sweat-damp tendrils of hair from your forehead, "The tightest, wettest, most mouthwatering pussy a squire could ever hope to find." 

You hummed through your broadening grin, tickled by his words, and kissed him one last time for good measure. 

* * *

After Sam had fixed his tux back to its original state, he gave you a dimpled grin and offered to help with the zip on your dress. Once he had it pulled up and you'd turned to face him, he gave you one long, slow head-to-toe once over, bottom lip trapped between his teeth as he shook his head like he couldn't believe it. 

"Damn," he said, eyes flicking back up to meet yours as he smirked all boyish and charming, "Just... _damn_." 

"Sam Winchester, everybody; the world's new up and coming poet," you smiled and rolled your eyes playfully. 

"See ya 'round, dirty girl," he bid farewell after a small laugh, one eye dropping down into a cheeky wink before he turned on the heels of his fancy, polished oxfords. 

Once he'd been gone for a good three or so minutes, you walked over to the table by the door and plucked a few tissues from the ornate holder that sat there, using them to clean between your legs the best you could until you could get to a bathroom. You dropped them in the trash bin nearby and moved to make your exit. 

"There she is!" Your father's chipper voice boomed once you'd made it down the hallway. He was at your side in seconds, curling a soft hand around your elbow and saying, "Come meet some of my colleagues, pumpkin." 

"Daddy," you try to pull away, "I actually was just heading to the—" 

"It can wait," he decided on your behalf, tugging you along and around a corner as he asked, "Have you been introduced to the Winchesters yet?" 

_Shit._ "The Win—" You stopped just short of repeating the name when you were met with four faces—one familiar and three not-so. 

"Pumpkin, this John and Mary Winchester, and their sons, Dean and Samuel," your father explained, oblivious to the fact that your cheeks were burning hotter than the sun and the sound of your heart galloping loudly in your ears. 

You looked to John and Mary, pulling out your old talent of faking it to plaster a smile on your face. "So lovely to meet you," you said, pointedly ignoring Sam and his knowing grin. 

"Y/N here just graduated top of her class at Berkeley," your father gushed, and it was then that you realized what this was—the age-old pissing contest. "She's been accepted into Yale Law School beginning in the fall. Yes, my girl is whip smart and destined to be the country's best." 

"Oh, daddy, stop," you feigned embarrassment, fake smile dropping a bit as you looked at him and said through gritted teeth in a faux-sweet voice, "Really, please stop." 

"Well, what a coincidence," the Winchester patriarch chimed in, "Sammy, too, just graduated top of his class—Stanford man, he is. He'll be attending Harvard Law in the fall. I'm sure Sam will be quite the competitor in the run for the title." 

Your stomach rolled. There really wasn't that much distance between Yale and Harvard, only a few hours, so you could easily get laid and laid _good_ if you—

"What fun!" Mary Winchester beamed, looking at her youngest son and then you and saying, "You two could get together sometime and talk law, since you'll be so close to one another." 

"Ha," you fake-beamed back, "Maybe." 

Your father and John fell into a slowly heating debate on whether Harvard or Yale was a better school, and you were only half listening to their talking points when suddenly—you felt _it._ Between your legs, where your pussy was still so sensitive and tender from use, a splodge of remaining cum leaked out of you and smeared wetley between your thighs. 

You gasped, eyes widening, and it caught the attention of the group, and with the last shred of your dignity that remained, you inconspicuously as possible crossed one ankle over the other, pressed your legs as tightly together as you could manage and said to the questioning faces around you, "If you would all excuse me for just one moment; I need to run to the ladies' and, uh,—" _wipe your son's cum off of me_ , "—powder...something." 

If you weren't ignoring Sam before, now you really were—you could feel his smirk of realization burning into the side of your head and you just barely held back the urge to flip him off. With one last grimacing smile, you carefully turned on your heels and began a speed walk towards the nearest restroom, mortified when you felt the sticky remnants of your and Sam's coupling slide down one of your inner thighs towards your knee. 

The group had watched you scurry off, thankfully all but one—really, two—utterly unaware of the reason for your strange exit. While John, Mary and your father made headway into a new conversation, Dean turned to Sam and sniffed in his direction in a rather dramatized way, adding the comment of:

Sam's face remained coolly neutral. "Correction, big brother," he replied in a low voice so only Dean could hear him, "I smell like the best sex I've ever had in my entire fucking life." 

"Sammy, you sly dog, you," Dean chuckled, turning his head to look in the direction you'd disappeared in. "And the girl that was just here, Y/N," Dean pondered aloud, bringing his attention back to Sam, "She beat a hasty retreat because—" 

"Yep," Sam dropped his head in a small nod, plucking a fresh flute of champagne from the tray of a waiter passing by, taking a small, normal-person sip. 

"Details, little brother," Dean grinned mischievously, "I want them all."


End file.
